


50 First Dates

by Gedry



Category: Supernatural
Genre: But only in one date, F/M, M/M, Multi, Sibling Incest
Language: English
Status: Completed
Published: 2017-11-02
Updated: 2017-11-02
Packaged: 2019-01-28 15:21:25
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 50
Words: 37,015
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12609600
Author URL: https://archiveofourown.org/users/Gedry/pseuds/Gedry
Summary: Each chapter is a new date.  Please see notes for prompts and pairings.





	1. Date 1:  Museum

**Author's Note:**

> 1\. Sam/Gabriel museum  
> 2\. Lucifer/Jo Wings  
> 3\. Sam/Cas Broadway  
> 4\. Dean/Gabriel Stars  
> 5\. Sam/Gabriel Flying  
> 6\. Sam/Gabriel Drinking  
> 7\. Dean/Cas Walk  
> 8\. Dean/Cas Movie Theater  
> 9\. Adam/Elijah Biking  
> 10\. Sam/Castiel Grace  
> 11\. Dean/Cas Sailing  
> 12\. Sam/Lucifer Clouds  
> 13\. Anna/Crowley Deals  
> 14\. John/Gabriel Disney  
> 15\. Dean/Castiel Good Night Kiss  
> 16\. Sam/Lucifer Skating  
> 17\. Dean/Cas Road Trip  
> 18\. Dean/Gabriel Blind Date  
> 19\. Dean/Cas Wedding  
> 20\. Dean/Cas Baby Animal  
> 21\. Sam/Gabriel Medieval Restaurant  
> 22\. Bobby/Crowley Japan  
> 23\. Sam/Gabriel Ren Fair  
> 24\. Dean/Castiel Bowling  
> 25\. Meg/Cas Making Out  
> 26\. Anna/Jo Chocolate Cake  
> 27\. Dean/Cas Morgue  
> 28\. Lucifer/Sam Rowboat  
> 29\. Cas/Dean or Sam/Gabriel Pet Shop  
> 30\. Dean/Gabriel Halloween  
> 31\. Dean/Gabriel Abandoned Kittens  
> 32\. Gabriel/Castiel Merry-go-round  
> 33\. Sam/Gabriel Drive in Movie  
> 34\. Sam/Gabriel Gondola ride Venice  
> 35\. Sam/Gabriel and Dean/Castiel Double Date  
> 36\. Gabriel/Sam Arguing  
> 37\. Dean/Cas Ice Cream  
> 38\. Dean/Cas/Gabriel Sushi  
> 39\. John/Gabriel ER  
> 40\. Cas/Sam Fishing  
> 41\. Dean/Cas Amusement Park  
> 42\. Dean/Cas 3rd Times a Charm  
> 43\. Dean/Cas Kissing in the Rain  
> 44\. Sam/Gabriel Watching Porn  
> 45\. Gabriel/Kali Juggling torches  
> 46\. Gabriel/Cas Superbowl  
> 47\. Dean/Cas/Sam/Gabriel (up to me)  
> 48\. Sam/Gabriel Living History  
> 49\. Gabriel/Kali All Hands  
> 50\. Sam/Gabriel Disneyworld

Title: Date 1  
Author: Gedry  
Pairings: Sam/Gabriel  
Rating: PG - 13  
Word Count: 1408  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.  
Beta: none  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – museum. 

Date 1

Sam sighs as he works his way through the crowds surrounding the mall area. The senior trip to the Smithsonian had been a much looked forward to highlight of his year up until he actually had to go. 

They got split into pairs for their last class assignment and he got stuck with Gabriel Novak. 

Sam hates Gabriel Novak; has hated him since grade school when Gabriel stapled Sam’s shirt to the desk on purpose and kicked sand in his face on the play yard. It only got worse from there. In middle school Gabriel stole his homework and made farting noises during Sam’s eighth grade speech for President’s Day. 

By the time high school started Sam’s daily life had involved trying to avoid Gabriel at all costs. He once gave himself a urinary tract infection by avoiding the bathrooms for fear of being locked inside them. 

So now, to be stuck with the joke playing jackass for two days is bad enough but to have his final grade be dependant on Gabriel actually helping with the work is adding insult to injury. 

“How about the air and space museum,” Sam offers; he’s hoping that something science fiction related might actually make Gabriel pay attention. 

“Nah,” Gabriel says as he works his way through a giant soft pretzel he produces out of nowhere. “I was thinking of heading over to the art one. Chicks dig art.”

It takes everything Sam has not to turn and stalk the other way. Not that he gives a shit about Gabriel’s interest in the female population of their senior class; Sam’s quietly identified himself as gay for as long as he remembers. 

So Gabriel can take his amber eyes and crooked grin and ram it up his own perky, tight little ass. 

Okay, so maybe the crush he has on his tormenter might be another part of the problem. 

“Art it is,” he grinds out with false smile and trudges along behind his classmate into the museum. 

Gabriel wanders aimlessly, not commenting on much until they work their way into exhibit on Faberge eggs. Then to Sam’s surprise Gabriel becomes and encyclopedia of information. He drolls on and on about how they were made and where they come from, he covers what they symbolize and how many there are in the world. He talks about their significance and impact on the art world at the time they were being made. Sam stands there furiously taking notes with his mouth hanging open in shock. 

“How do you know all this shit?” he finally asks when Gabriel takes a break to breathe. 

He has to be imagining the blush growing across Gabriel’s face. 

“My mom’s an art teacher at the community college,” Gabriel shrugs. “I’ve always liked these things. They’re beautiful and complicated and they remind me of food and I love to eat.” 

Sam laughs. He thinks it might be the first time Gabriel has done something funny around him that hadn’t made him the butt of the joke. 

They take a few pictures, makes some more notes and head back out to where the group is starting to pile up waiting for the trip back to the hotel to start. 

“Sam!” Andy exclaims as he runs up to his friend. “You’re never going to believe it but Madison likes me. Like really likes me. So I’m switching seats on the bus you’re going to have ride back with Becky.”

“Oh fuck,” Sam groans as he rubs at his face. Becky’s been after him since she moved into town in the eighth grade and short of humping a guy in front of her nothing has convinced her that Sam’s not interested. 

“Sit with me,” Gabriel offers quietly. “I’m not sharing.”

It’s true too; somehow Gabriel got the only single in the whole class. Sam blinks at him stupidly. 

“No joke,” Gabriel blurts with his hands raised. “I swear. I just know she drives you nuts and I figured for once you might think I was the lesser of two evils.” 

Sam ends up pressed between Gabriel and the window as they pull out, Becky glares at him the whole ride back and Sam struggles to keep a straight face as her attention just seems to make Gabriel act out in worse and worse ways. 

By the time they get to hotel Sam’s exhausted and starving but money is always tight for his family and Dean worked two jobs all winter just so Sam could afford to go on this trip. He eats the couple of free packages of crackers he stole from the last restaurant they were in and figures that will hold him until morning. 

Then there’s a knock on the door of his room. 

“Gabriel?” Sam sputters as he sees his classmate holding up a pizza and a little white napkin folded like a flag. 

“I know we don’t have the best history,” Gabriel offers. “But I was hoping you wouldn’t make me eat this thing alone.”

Two hours later their presentation is as good as it’s going to get without Sam obsessing over it. Gabriel’s sprawled across the bed next to him with the now empty pizza box tossed onto the floor. 

“I’m not an asshole, I swear,” Gabriel announces while Sam looks for something to watch on TV.

“Could have fooled me for the past ten years,” Sam says before he thinks it through. He winces even as Gabriel does the same. 

“I’m really shitty at courting,” Gabriel sighs dramatically. “But I promise I’m a much better boyfriend. You’ll see.”

“Do what?” Sam asks as he watches his world tilt off it’s axis right in front of his face. 

“You have no idea what it took to get Singer to assign you to me as a partner,” Gabriel answers excitedly. “And then to get Madison to actually swallow her pride and make a move on Andy. She’s liked him forever but has this thing about the guy going first. He was never going to do that so I pushed her. The bus driver cost me fifty bucks to get that seat by myself. I’m working my ass off here Sam, the least you could do is keep up.”

“You like me,” Sam whispers with a tinge of awe in his tone. “All these years that was you trying to get my attention?”

“I’m an idiot,” Gabriela admits. “In my defense you never gave me an inch to work with Sammy. I wasn’t sure enough about you to just put myself out there and you’re like completely asexual.”

Sam has flashes all of a sudden about the times when his mind would produce fantasies of Gabriel while Sam was touching himself and considers how wrong Gabriel is about that assumption. But Sam damn sure isn’t going to tell him that; not today.

“You were scared,” Sam concludes. “Why now?”

“I’m running out of time,” Gabriel says softly. “School’s almost out and I don’t want to be trying to make out with you at our ten year reunion and bitching because we wasted so much time. I want to make out with you like every day until our ten year reunion.”

He leans forward then and Sam jerks back out of his reach. Gabriel pinches his lips together tightly and nods before slipping off the bed to go back to his own room with his shoulders slumped in defeat. 

“I don’t kiss on the first date,” Sam says as he reaches the door. 

Gabriel turns warily and Sam feels a tingle of joy that he’s managed to finally put Gabriel on edge like he’s always been. It’s wrong but so help him it feels too good. 

“What about the second date?” Gabriel asks softly. 

“Try me and we’ll see,” Sam answers with a smile. 

He rides back home on the bus pressed between Gabriel and the window. Becky’s still glaring but Sam doesn’t care. Gabriel’s knee is pressed up tightly to his own and Sam’s brave enough to reach out and wrap his pinky around Gabriel’s under the coat they have shoved between them. 

He’s looking forward to Gabriel proving how good a boyfriend he actually is.


	2. Date 2: Wings

Title: Date 2  
Author: Gedry  
Pairings: Jo/Lucifer  
Rating: PG - 13  
Word Count: 1075  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Wings. 

Date 2

She’s going to have glue in her hair for the rest of her life and she knows it. 

How Jo was ever conned into helping the Novak boys with their assigned jobs for the school play she will never know. It’s been a week of tugging and pulling and tape stuck to her body in the weirdest places. 

“Tell me again why we couldn’t just go buy wings on a harness?” she whines after two hours of standing perfectly still in their living room while they tuck and pluck feathers into the appendages she has strapped to her back. 

“It wouldn’t look authentic,” Castiel comments. 

“It wouldn’t be fun,” Gabriel adds.

“Fuck you both,” she groans but she makes no move to leave. These guys are her friends, they have been for years and maybe if she hangs out long enough she might get a glimpse of their older brother coming home from community college this evening. 

Lucifer graduated last year and Jo misses seeing him at school every day. There’s something about his closed off but well mannered attitude that makes the girl in her that’s from the wrong side of the tracks scream for attention. 

She’s a senior now, she’s eighteen, and she can lust after the nineteen year old, high school graduate, older brother of her friends with no need to be ashamed about it.

“Okay,” Gabriel announces with a flourish. “Two hours fro now we’ll be done! An angel will be born!”

“Great,” Jo agrees with a mixture of relief and disappointment. “Help me take it off.”

“You can’t,” Cas says seriously, like they’ve discussed this already and she’s crazy for not understanding the plan. “You have to stay here wearing them, standing up or they will lose their shape.” 

“I hate you,” Jo snaps. “I hate you both so much right now.” 

It only takes about a half hour before they leave her to seethe in peace. Gabriel has the attention span of a gnat and Cas has homework to do. 

Lucifer finds her stuck in the middle of the living room with her arms crossed and her back aching thirty minutes later. 

“Joanna?” He questions as he drops his bag and carefully steps closer to her. “Are you alright?”

“Your little brothers are idiot dicks,” she announces then clamps a hand over her mouth and closes her eyes in humiliation. It’s like being around Lucifer gives her some kind of horrible Tourettes syndrome. 

But he laughs, a warm and rarely heard sound before agreeing: “That they are. This is for the play I assume?”

She nods, blushing as she realizes that she’s wearing a sports bra and nothing else trying to keep paint and glue off her clothes. She doesn’t have that many shirts to spare. 

“It never occurred to them to use our mother’s clothing dummy in the attic did it?” He asks as he plucks at a feather in her hair. It’s stuck and she winces making him hiss as he realizes he’s hurting her. “Then they left you here by yourself?”

“They’re upstairs,” she offers. “I have another hour before I can take it off.”

His look tells her everything she needs to know about how he feels about that. Her hair tumbles over her shoulder as he finally gets the feather loose and she shivers in response. “You’re cold,” he blurts when he sees the goose bumps pebbling her skin. “Here.” 

Then he’s sliding off his zippered sweatshirt and tugging it up her arms backwards until it’s tucked up under her chin. It smells like Lucifer and it’s so warm she can’t stop the happy sigh that slips out. 

She blushes when she realizes he’s standing so close to her and he seems to shake off something he’s feeling before asking “Hungry?” 

He ends up bringing her cereal. She tries not to be too unladylike as she snarfs it down. She’s starving. 

With twenty minutes to go the pain in her lower back reaches a point where Jo’s ready to rip the wings off no matter how badly they might be ruined. She didn’t sign up for this. 

“Do you dance?” Lucifer asks softly from where he’s been hovering near the doorway to the living room. 

“Not really,” Jo mumbles. She’s a bar owners daughter. Guys tend to assume she’s unapproachable or easy. Dancing’s never been her thing. 

“Here,” Lucifer says as he comes around in front of her again. “Lean on me and I’ll teach you. It will take your mind off your back.” 

He’s taller than she thought he was, her head pressing into his neck as she loops her arms around him. His hands are warm on the skin of her back. 

She jerks when he touches her there; she forgot she wasn’t wearing a shirt with the protective cover of his jacket. 

Just changing positions to let him take on some of her weight makes a world of difference and she groans out her appreciation making his chest vibrate with soft chuckles as he holds her close. 

It might be hours later, Jo’s not really sure when Castiel and Gabriel suddenly reappear and start tugging off the harness. 

She stumbles back out of the bathroom feeling a little less exposed with her shirt on. 

“Let me give you a ride home,” Lucifer offers. They make it as far as three blocks before he pulls the car over on the side of the street and grips the wheel tightly before asking: “Do you have to be home right now?”

“No,” Jo says softly. “It’s my day off. I’ve got until ten.”

“Have dinner with me?” Lucifer asks, or orders, it’s sometimes hard to tell with him. 

“I just ate cereal,” Jo answers and then wants to choke herself to death. 

But instead of throwing her out of the car he laughs until there are tears in his eyes. She can’t help but smile in return when he reaches out to touch her hand with his fingertips. 

“Then just hang out with me for a while,” he says as he brushes over the back of her hand and across her wrist. 

“Like a date?” Jo asks. 

“Yes,” he grins. “Exactly.”


	3. Date 3: Broadway

Title: Date 3  
Author: Gedry  
Pairings: Sam/Cas  
Rating: PG - 13  
Word Count: 710  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Broadway. 

Date 2

“Dude,” Dean grumbles. “A play? How gay is that?”

Sam glares as hard as he can at the back of his brothers head. “Well being that I’m going on a date with a GUY I guess it’s a little bit gay Dean!”

“Cas isn’t a guy,” Dean waves him off while he keeps on playing his stupid Wii golf game. “He’s – Cas I guess. I dunno.”

For the thousandth time Sam tells himself this is fucking horrible idea. Why of all the people in the world does he have to have the hots for Dean’s weird, socially inept, best friend? 

This is going to end bloody for all of them. 

There’s a knock at the door and Sam yanks it open to find Cas standing on the other side with his hands in the pockets of the weird looking almost velvety jacket that he’s wearing. 

“Since when do you knock?” Sam blurts. 

Cas actually flinches before he offers: “I’m not here for Dean this time. It felt more appropriate for me to announce myself.”

“Oh,” Sam whispers right before Dean snorts “Whatever Cas. It’s just Sam. It’s not like he’s hot or anything.”

Dean never takes his eyes off the screen which is probably how he misses Cas’ eyes dilating so far that his unique color of blue is blurred away by blackness. 

Sam’s dick is suddenly so hard he could hammer nails with it and he remembers why he suddenly cracked last week after months of pining to beg Dean for his acceptance of Sam breaking their very strict rules about dating and friendship. 

Cas is hot, Sam has to have him. 

*****

The place is packed and Sam’s crammed in the seat like he’s going to need a shoehorn to pry himself out later. Intermission is almost over when Cas says “Are you having a good time?”

Sam’s not, and it’s not the company that sucks. He likes culture. He enjoys art and low budget, high brow films with subtitles. But really what he wanted tonight was to get Cas to himself for more than just a few stolen moments in the kitchen while Dean goes to the bathroom to take a piss. “It’s good.”

Cas’ eye twitches. “You hate it.”

“No!” Sam blurts a little too loudly as people turn around to glare at him as the lights go dim. “No,” he whispers. “I just was kind of hoping we would get a chance to…talk tonight. I want to be selfish and get to know you without Dean around.”

He might be imagining the pick flush traveling across Cas’ cheekbones but there is no mistaking the way the other mans hand slides across his leg to curl around his inner thigh. 

Oh, it feels so good to be touched. Sam’s tactile and his last date was months ago, his last relationship even longer than that. It’s taken him a while to get back into the game after that very nasty break up. 

He has to stop himself from pushing farther into the heat of Cas’ palm and purring like a giant idiotic cat. 

Cas’ thumb drags back and forth across his thigh as his eyes stay glued to the stage. 

“When this is over,” Cas whispers. “We’ll get a late meal and then you can keep me up until sunrise telling me everything and finding out whatever you want.”

“I want everything,” Sam answers even though he knows it’s pissing off the people sitting to the other side of him. He doesn’t care because he really does want to know everything Cas will tell him. 

He wants to know the things Cas hasn’t told anyone.

He reaches over and caresses the soft skin of Cas’ wrist while Cas keeps a steady, soft rhythm of contact between their bodies. It’s grounding, settling for Sam to be linked to him like this. 

“Me too,” Cas whispers back with a grin Sam can see curving around his mouth. 

Sam smiles too. This is going to be perfect.


	4. Date 4: Stars

Title: Date 4  
Author: Gedry  
Pairings: Dean/Gabriel  
Rating: PG - 13  
Word Count: 549  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: moonofblindness  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Stars. 

Date 4

It’s something Dean’s done for as long as he remembers. He gathers up a blanket and wanders his way out into the middle of the field he found just outside of the county lines. When he was smaller it was harder to get to places like this. His mom screaming at him all hours of the night when would slip from his bed and crawl up onto the roof to look up at the sky. 

Dean’s afraid of flying, but the stars have always felt like home. 

He’s never asked anyone to come with him before. Not even Sam. So having Gabriel trailing behind him with a cooler and another blanket gives Dean a mix of feelings that he’s struggling to put names to. 

If they were stars he would know their names. He knows all the stars names. 

“So this is it huh?” Gabriel says quietly as they spread the blanket out and settle down into the soft grass. 

“Yeah,” Dean answers looking up toward old friends that never failed to be there when he needed them as he thinks about this new friend at his side that he wants so much to depend on too. “This is it.”

They stay sprawled on their back in silence for a long time until Gabriel shifts slightly and the back of his hand bumps up against Dean’s. “You know,” Gabriel comments. “When you asked me to come star gazing with you this isn’t what I thought you meant.”

“What did you think I meant?” Dean asks as he turns to look at his friend curiously. 

Gabriel bites his lip and struggles to keep a grin off his face before he answers: “I thought you were asking me to sneak off and have sex with you.”

“GABRIEL!” Dean erupts as he launches himself into a sitting position. “Are you fucking kidding me?”

“No,” Gabriel blurts. “How was I supposed to know you were like a closet geek? I’ve only been in town for three months and no one ever said anything about the fact that you can name all the freaking constellations.”

“Fine,” Dean growls as he pushes himself up off the blanket and digs for his keys. “Forget it. I’ll take you home. I’m sorry I’m not what you expected.”

“I’m not,” Gabriel answers as he refuses to move off the blanket no matter how hard Dean tugs on it. 

“What?” Dean asks. 

“I’m not sorry,” Gabriel answers. “This is a big deal to you. Sex wouldn’t have meant anything. If no one knows about this and you brought me out here then that is a big deal. It means you really like me. Maybe enough to want me to stick around and that doesn’t happen to me that often so I’m going to sit here and you’re going to teach me the difference between the little dipper and Constantinople.”

“Cassiopeia,” Dean corrects. “It’s Cassiopeia.”

“Exactly,” Gabriel says with a wave of his hand. “See I’m learning something already.”

Dean stops glaring when Gabriel kisses him.


	5. Date 5: Flying

Title: Date 5  
Author: Gedry  
Pairings: Sam/Gabriel  
Rating: PG - 13  
Word Count: 715  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Flying. 

Date 5

Sam’s not a bad brother really. He’s not, he swears. 

But flying with Dean is enough to drive anyone to drink and okay, so slipping him something to knock him out was cold hearted but it makes the next leg of their trip semi bearable for Sam who’s already suffered through eight hours of flying to get to this stupid wedding. 

Why the hell did they tell Jo they would come? She live across an ocean for fucks sake and watching Dean hug his seat cushion like a floatation device is not nearly as funny as it sounds. 

His brother is such a pussy. 

“So,” the guy sitting next to him comments. “Did he get drunk on the layover or did you drug him?”

“What are you talking about?” Sam hedges as he leans away. The guy’s smaller than he is but really at this point who isn’t? He’s got greenish, maybe goldish eyes and amber hair. For a little thing he seems to eek out confidence. Sam’s a little jealous of that actually. 

“I was on the last flight with you two,” he answers. “Three rows back on the other side of the isle. Your brother was hyperventilating and swearing he wasn’t even going to get on this plane. Now he’s sleeping like a baby. So either you took him out and got him trashed or you dosed him with something to make him sleep like a baby. I’m not judging you; it’s a solid plan. I’m just curious. My name’s Gabriel by the way.”

“Sam,” he answers. “I drugged him.” He has no idea why he’s telling this guy the truth.

“Awesome,” Gabriel chuckles. “I wish I could do that to my brother sometimes but frankly he’s so laid back I’m afraid it would kill him.”

Sam grins. He can’t seem to help himself. 

“Long flight,” Gabriel comments. “You got plans or something to work on?”

“No,” Sam answers with a shake of his head. He figured he would have to spend the whole time talking Dean down from the ledge. When he packed the sedatives he hadn’t actually thought he would use them. “I’m open.”

“Good,” Gabriel smiles. 

They spend the next six hours getting to know each other better. Maybe it’s something about the anonymity of the fact that they are probably never going to see each other again or that Sam finds out during their conversations that he actually really like this Gabriel guy. 

But when the plane’s landing and Sam is hauling his still knocked out brother down the isle he sure doesn’t turn down Gabriel’s offer to help him through customs. 

The fact that it means a little bit more time with the smaller man has nothing to do with it really. 

Sam finally gets Dean settled onto a bench once they get things finished and when he turns around Gabriel’s gone. 

Sam certainly does NOT spend the next week obsessing over a guy that he’s never going to see again. 

Not even for even a second. 

The flight home is looking to be just as nasty and Sam’s already in a perma-foul mood due to his obsession with the one that got away. Dean being awake and bitching doesn’t help either. 

“You don’t want to sit here,” a voice says to the woman in the seat next to Sam. “These guys are a mess. Here, I’ll trade you. You can take my seat in first class and I’ll suffer through the flight with Thumper and Bambi.”

The woman almost knocks Gabriel down when she gets out of the seat. He winks at Sam as he plops down next to him and puts his seat belt on. 

“Who the fuck are you?” Dean asks. 

“Your brother’s boyfriend,” Gabriel answers while Sam’s mouth falls open. “We met while you were sleeping.” Then he turns to Sam and smiles. “I missed you. Good thing your name and address are on your luggage. My brother works for the airline.” 

Sam holds his hand most of the flight home.


	6. Date 6:  Drinking

Title: Date 6  
Author: Gedry  
Pairings: Sam/Gabriel  
Rating: PG - 13  
Word Count: 526  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Drinking. 

Date 6

“You never get stood up do you?” Gabriel growls at the waiter that comes by to take the order he’s not placing. The guy’s young and too damned tall to be human. Big hands too and Gabriel wonders absently if he’s built proportionately. 

The kid turns pink; maybe he said that out loud. Fuck it; he doesn’t remember what drink he’s on anyway. 

“Never mind,” he comments with a dismissive wave of his hand. “Bring me another.”

“Don’t you think you’ve had enough?” the waiter asks. But when Gabriel glares he comes back with a fresh glass of wine. It’s not the mixed drink he was inhaling but it’s better than nothing. 

Cas can’t pick him up until he closes the shop in two hours so Gabriel figures he’ll get nice and hammered while he waits for his designated driver. Hell, being stood up is something to drink on he’s pretty sure. 

The rolls appearing at his elbow make him twitch but by the time he turns around there’s no one standing there. The next time his glass is empty it gets replaced by a glass of soda and a steak he doesn’t remember asking for. 

It’s fucking good though so he doesn’t complain too much. 

Lonely, but Gabriel’s getting a little used to that sadly. He’s facing down forty pretty quickly and he’s starting to think he’s going to land on it alone. 

He’s feeling pretty well sober when his waiter reappears wearing a sweatshirt and a pair of blue jeans carrying a bowl with a huge brownie on it smothered by ice cream and chocolate sauce. 

“I think I’m in love,” Gabriel murmurs when the kid slides into the booth across from him where his date is supposed to be seated.   
“My name’s Sam,” the waiter announces. “And to answer your previous questions, yes I do get stood up sometimes. And yes it is proportional.”

Gabriel flushes with horrified embarrassment. “I’m so sorry.”

“Look,” Sam shrugs. “My brother is supposed to pick me up in a half hour. I usually grab something to eat after my shift ends; which it has as of five minutes ago. So I can go hang out with my buddies in the kitchen or I can share this brownie with you. I promise, I’m a much better date than whoever you were supposed to be meeting and frankly you’re hot and I’m into older guys. So what do you say?”

Gabriel blinks. This can’t be real. “No shit?” He asks because he is totally not that lucky.

“No shit,” Sam assures him as he holds up two forks and grins. It’s a nice smile, a smile Gabriel could get used to seeing. 

“Call your brother, I’ll call my brother and then hand me that fork,” Gabriel orders. “After we’re done you can drive us both home in my car.” 

It’s a fucking good brownie.


	7. Date 7:  Walk

Title: Date 7  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 535  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Walk. 

Date 7

Dean’s walked with guys before. You know, like going to the bar or carrying furniture when they’ve moved. He’s been a great wing man for a few people, like Sam, who mean a lot to him and deserve the very best. 

Walking now isn’t really like those moments, where he either led or followed with security. 

Cas makes him nervous. It was his first sign that this guy, THIS guy was something worth pausing and paying attention too. Dean’s never been one to want to put too much effort into things. He plays his cards close to his chest and keeps his feelings balled up in the back corner of his car to shovel the dust and dirt off one day and examine when he has the time and the inclination to discover more of himself. 

Cas makes him want to learn, explore things in a way that Dean thinks might just leave him being a better person if he was willing to try. 

So when Cas suggested they take a stroll, well Dean wasn’t going to say no to him. He’s a little out of his depth but Dean’s never been one to run from a challenge. 

Still though, he might like to hold Cas’ hand if the dude would ever take them out of his pocket and if Dean thought that maybe that’s what he wants too. 

Cas is fucking hard to read sometimes. 

So they’re walking, looking at the trees in this park that Cas’ apartment is by and listening to the birds chirp and the trees rustle as the wind blows. Cas isn’t really looking at him much and Dean spends much of the first part of their stroll a few steps ahead and looking around as he wonders if he should risk it and see what happens when he dusts off his heart. 

So he stops quickly and smiles as Cas’ body plows into his back, the other man’s breath a huff of surprise before Dean looks at him over his shoulder and smirks. 

Cas grins back, his eyes twinkling in the light. 

They walk a few more paces and Dean does it again, and again, and AGAIN. 

The last time though Cas shoves him forward with a chuckle and then steps around Dean like a dancer before taking the lead. 

Nothing happens for a while and Dean spends a lot more of his time staring at the other man’s ass than at the park they are wandering through. 

But then Cas’ hand is sliding out of his jacket pocket and reaching behind him for Deans. 

Oh yeah, Dean smiles as he almost dances with relief. This could be the start of something wonderful, something that heals him. 

Cas’ hand is warm when Dean threads their fingers together, so is his smile, his eyes, and Dean suspects his heart. 

They don’t have a destination in mind and that makes their journey that much sweeter.


	8. Date 8:  Movie Theater

Title: Date 8  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 603  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – movie theater. 

Date 8

How they ended up coming here on foreign language film night is a testament to how much Dean really likes Castiel Novak. 

He REALLY likes him. 

So instead of watching something cool, possibly car or comic book related, Dean slouches back in the high seats of their local movie theater and pretends that he understands what the hell is going on up on the screen. 

He knows Cas is taking French level five hundred or something this semester but Dean failed German once in high school and Latin twice before he and language decided that they were in an unhealthy relationship and parted on good terms. 

Sometimes when you suck you just have to come to terms with it. 

Cas is sitting beside him, rigid, like he just swallowed a broom. Dean swipes his sweaty palms on his jeans and shifts a little bit closer to his friend. 

He likes Cas, has for a long time. Cas likes him too, he’s the one that told Dean he thought Dean was attractive in a more than buddy way. It was brave of his roommate. Dean’s been toying with the idea that he’s not exactly uninterested in guys for a long time but actually taking that step into dating one was something he had never done before three days ago when Cas made his confession and Dean blurted out ‘Come to the movies with me.’ like it was the answer to all their problems. 

So really, it’s a movie date. It can’t possible be that different than dating a girl. 

In theory Dean’s set, in application he’s lost. 

Should he hold Cas’ hand?

Should he do the old reach around and try to put his arm around him?

What about stealing a kiss?

Maybe he should just reach out and touch his leg?

Jesus, why is this so complicated?

Dean opts for the chickens’ way out and does nothing until the movie ends and they wander out into the lobby. 

“It was interesting,” Cas comments. 

“Um,” Dean sighs. “Honestly I was kind of lost the whole time.”

Cas’ eyes squint in what Dean suspect might be full blown horror on someone more animated. “You’re not having a good time.”

“No,” Dean blurts as he shakes his head. “Look, I’m just really confused. I’m not sure what to do with you. I mean this is date right? Then it’s supposed to be more than two guy friends sitting beside one another in the movies.”

“The problem?” Cas asks with his head tipping to the side. 

“I don’t know how to make it more intimate,” Dean tries for a fumbled hand gesture that doesn’t help explain things at all. 

Maybe sock puppets next time assuming Cas will ever go on another date with him. 

Cas looks over Dean’s head for a moment with squinted eyes. “There’s a showing of Red Riding Hood in twenty minutes. Do you want to go to see that?”

“Not really,” Dean chuckles. “Is it all we’ve got?”

“I’m afraid so,” Cas mumbles. “But I can assure you that you won’t remember half the movie at least when it’s over.”

“Why not?” Dean asks as he follows Cas to the ticket line. 

“I’ll have my tongue in your mouth,” Cas announces like he’s commenting on the weather. “And if you’re really lucky, my hand in your pants.”


	9. Date 9: Biking

Title: Date 9  
Author: Gedry  
Pairings: Adam/Elijah  
Rating: PG - 13  
Word Count: 731  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Biking. 

Date 9

He swallows another scream as the bike slams down over the ledge and races head on after the other boy in front of him. His knuckles are white he’s gripping the handle bars so tight and his arms are shaking from the strain. 

He’s not even going to mention how badly his knees are screaming at the multiple impacts of going over rough terrain or the fact that he can now officially hear his heart beating in his ASS. 

Elijah is a city boy. It’s not something he’s ever been ashamed of. He knows he falls into that category of gay man that other people refer to as effeminate. He wears button down shirts all the time, styles his hair every morning, gets his nails done and he’s not opposed to eye liner if it adds and extra pop. He and his two more accepting older brothers go for monthly pedicures. 

So fuck him, that’s his life and he’s learned to dig up under a parent load of seriously right wing religion to love himself enough to accept he’s never going to be a man’s man. 

So why the hell he developed the hugest crush in the history of the world on Adam Milligan-Winchester of all people is beyond him. 

The Winchester’s are like testosterone on testosterone with a heaping side of testosterone. Their dad is the high school football coach. Dean runs a auto body repair shop on the edge of town focusing primarily on beat to hell vintage vehicles. Sam is away at college but still he’s fucking HUGE!!! 

Then there’s Adam, the youngest of the group from John’s second marriage. He’s softer, a little blurred around the edges of his masculinity in a way the others in his family clearly are not. Elijah’s had the hots for him since they hit town three years ago but at the time he was still deciding if his parents were right about fags going to Hell and hadn’t wanted to drag anyone with him just in case. 

But then Adam had actually paid attention to him! After three months of unbearably awesome flirting Adam has finally asked him out and Elijah had lost utter control of himself in agreeing. 

Hence racing down the side of a mountain on an itty bitty bike with no clue where they were headed or how to stop. Who the fuck goes mountain biking for their first date anyway? First dates are made for intimate dinners and holding hands, learning the scent of your new love interest and finding comfort in leaning into their personal space. 

First dates are for kissing with music swelling in the background while everything in the world fades to black. 

Okay….so Elijah’s been watching too much Twilight, clearly. 

But still; how the fuck is Adam going to kiss him when he’s like two miles ahead of him out here in Hillbilly Hell. 

Oh, there’s the car. How did that get there?

“Normally we walk back up,” Adam chuckles at Elijah’s bug eyed expression. “But I kind of thought you might have been ready to stop for the day so I asked Dean to move it for me on his way to work with Uncle Bobby.”

“I’ll have to bake your brother something,” Elijah mumbles as he tries to get off the bike and nearly falls over. 

“He’d like that,” Adam snorts. “So long as it’s totally platonic. I don’t want him getting the wrong idea. I’m planning on keeping you.”

Maybe it’s the pain that’s slowly spreading all over his body, maybe it’s the heat and his lack of water, Elijah might never know. But one second he’s trying hard not to fall over and the next he’s gotten Adam pressed against the hood of his beat up little car molesting his mouth for all it’s worth.

There’s no music, they both are filthy and stink terribly, Elijah ponders that he might be crippled tomorrow but then Adam slides rough hands up the back of his drenched t-shirt and sticks his tongue into Elijah’s mouth. 

After that he forgets everything but how much fun he’s having.


	10. Date 10:  Grace

Title: Date 10  
Author: Gedry  
Pairings: Sam/Cas  
Rating: PG - 13  
Word Count: 581  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: moonofblindness  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Grace. 

Date 10

Grace.

It’s something Sam’s never had. He’s not sure if it’s the growing up too quickly and having limbs too long to know what to do with before he was ready or if it’s just his nature to be a klutzy dumb ass. 

Either way he’s not graceful, never has been. Maybe that’s why he admires it so much. 

Castiel Novak is a different story all together. Sam’s been watching him for what feels like years. He has this intrinsic grace about him that makes everything he does look well planned out and perfectly executed. He never trips or knocks over soda cans, he doesn’t stumble through classroom doors or get stuck trying to get out of his seat. Sam once fell going up the steps to the advisory office in front of him and hit Cas on the way down. You would think someone Sam’s size falling on you would make anyone flail but Cas took the blow and steadied himself by pulling balance from out of nowhere before helping Sam get back to his feet. 

He’d bloodied and elbow that day and ruined one of his best shirts. Life is that way sometimes. 

To Sam the most fascinating thing about Castiel is that the guy manages to avoid all these things and be totally clueless at the same time. He reminds Sam of that part in Beauty in the Beast where Bell is reading the book and destroying the town. 

Except here Sam is the one destroying the town and he knows it. Castiel just managed to obliviously avoid getting hit by the wake of destruction Sam leaves when he goes. 

And we’re not going to talk about the fact that Sam likes that movie. 

“Lunch?” Castiel says as he walks up to where Sam’s slouched in the corner of the student lounge on their campus. 

“What?” Sam sputters. 

“I borrowed my brother’s car today,” Castiel explains as though Sam knows that he usually catches a ride with someone instead of driving. Which okay, Sam does know but it’s not something he advertises. 

He’s not stalking the guy….much.

“Good for you,” Sam mumbles because he and Castiel haven’t really talked at all….ever.

Castiel sighs like Sam is working his last nerve. “You’ve been watching me every day for over a month. I am making the assumption that you’re interested in me or my body at least. I thought getting to know one another might make it easier for both of us since you clearly want me and I’m getting tired of acting like I don’t notice. It’s hard to walk this straight all the time.”

“So lunch?” Sam manages to get out while he waits for the floor to swallow him up. 

“Yes,” Castiel grins. “You can pay and I’ll drive. No offense intended but you can barely control your own body much less a vehicle.”

Sam sputters with horrified laughter and Castiel reaches out to brush the hair from his face. “Yeah,” Sam whispers as his eyes slip shut at the warm, soft touch. “You should drive.”

Castiel makes a hum that sounds a little bit like happy contentment. He holds Sam’s hand all the way to the car. 

Sam doesn’t trip one time.


	11. Date 11:  Sailing

Title: Date 11  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 551  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: moonofblindness  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Sailing. 

Date 11

“Aren’t we supposed to be rowing or something?” Dean asks as he watches Cas settle back in the very tiny boat they shoved off the dock about fifteen minutes ago. 

“Only if you want to go somewhere,” Cas answers with a speculating look. “Do you want to go?”

“What?” Dean asks. “No. I mean I just sort of thought this would be athletic. You’re kind of always moving.”

“It’s my job,” Cas chuckles. “Or rather our job. You don’t sit still much either.”

Touché. 

But then this summer gig as a camp counselor is sort of like that. They wrangle the children all day and sometimes all night long and Dean’s not even trying to consider what he’s going to owe Ash and Jo for taking over for him and Cas tonight so they can go out on a….date. 

OH God. Dean’s on a date…with a guy. How did that happen?

“Looks like you finally bought a clue,” Cas comments as he stretches his legs out far enough that his bare toes brush the hair on Dean’s shin. It makes him shiver, makes him want to touch more. 

“We’re on a date,” he says stupidly. 

“Yes,” Cas grins. “Are you having a good time?”

And he is. He really is. It’s been fun hanging out with Cas tonight. Sure he’s been attracted to the guy since he rolled into camp the first day and they got paired up together. But Dean’s never crossed that line between attraction and romance with another male yet. Seems a little like Cas has been ahead of him on this one. 

“Yeah,” Dean settles on saying with a smile. “So we just float around out here in the dark?”

“That was the plan,” Cas sighs as he looks around. “As much as it’s a horror movie cliché for us to be out here alone together there is no other place for us to be alone without the kids barging in.”

“Well,” Dean assures him “If Mrs. Voorhees jumps up out of the water I promise I’ll protect you.”

“Who?” Cas asks. He’s clearly confused. 

Dean laughs. “Never mind.” 

They share a few moments of silence before Dean settles back on his side of the boat and lets the slight rocking motion relax him. His legs stretch out until they touch the outsides of Cas’ thighs. It’s comfortable, he feels like he fits here nicely with this sometimes distant, sometimes odd other young man. 

Then Cas reaches down and starts to massage one of Dean’s bare feet. The startled groan of pleasure Dean lets loose probably sounds like they actually are being murdered. 

Cas’ laugh is rich and Dean chuckles at himself even though he’s totally embarrassed. 

“I like you a lot Dean,” Cas says conversationally as he switches to Dean’s other foot. 

“I like you too,” Dean answers before ghosting his fingertips over Cas toes. He’s not really into feet but it’s the only part of his date he can reach easily. 

Cas’ toes wiggle against his fingers and Dean smiles.


	12. Date 12: Clouds

Title: Date 12  
Author: Gedry  
Pairings: Sam/Lucifer  
Rating: PG - 13  
Word Count: 589  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – clouds. 

Date 12

“That one looks like a Claudia Shiffer,” Sam comments as he points up at the sky. 

“You are a fucking idiot,” Lucifer grumbles off to his left. 

Sam falls out with laughter. He’s vindicated when Lucifer joins in. The guy just flat out doesn’t laugh enough. 

“How about Venus De Milo?” Sam asks. He gets the reaction he’s hoping for and Lucifer curls on his side facing Sam as he hisses with barely contained laughter. 

“I hate you so much,” Lucifer complains. “You know my ribs still hurt.”

“That’s what you get for trying to beat down two guys twice your size at that bar in Florida,” Sam chastises gently. 

‘Come across the country with us,’ Dean had said. ‘Just the four of us. It will be great all kinds of that bonding crap you love so much.’

Of course Dean and Cas decided halfway through the trip that they wanted to take bonding to the next level and now Lucifer and Sam are splayed on their backs in the grass watching the clouds go by while their brothers work off some energy with a nooner. 

It’s actually kind of fun. Lucifer’s got a better sense of humor than everyone gives him credit for. 

“You’re hot you know that,” Lucifer comments. 

Sam rolls his head toward the other man but Lucifer looking up at the clouds moving slowly through the sky. “Pardon?” Sam asks. 

“You,” Lucifer shrugs. “You’re attractive.”

“Umm,” Sam’s lost. “Thank you?”

 

“I mean it,” Lucifer sighs as he turns on his side and looks Sam over. “You get hit on all the time, you flirt but you never take anyone up on their offers. You never pursue anyone. Why is that?”

“I don’t know,” Sam shrugs. “I’m a big guy. Being aggressive makes me look like a Neanderthal I guess. I’m not really interested.”

“I don’t believe you,” Lucifer huffs and reaches out to poke Sam in the center of his shirt. 

“Fine then don’t,” Sam snaps and looks back up at the sky. 

Well he looks until he can’t see the sky around Lucifer’s encroaching head. 

“What are you doing?” Sam hisses as Lucifer pins him in with both his arms. He’s not nervous, Lucifer is tall but Sam’s the tallest thing around usually and even though he’s still filling out his ever expanding body he’s pretty certain that he could shove Lucifer off him in a heartbeat. 

If he really wanted to.

“Kissing you,” Lucifer answers and then he dips down and proves his point. 

The clinging that Sam’s doing to the back of Lucifer’s shirt probably isn’t making a good case that he wants to be let go. Neither is the way his hips jerk off the ground to roll against the other mans. 

Fuck it’s so good to be kissed. Sam hates dating, he hates having to manage everything about the early process of relationships. Honestly he just doesn’t really like being in charge. So the opportunity that Lucifer is giving him right now is very welcome indeed. 

Especially considering what Dean and Cas are probably doing in the car right now. 

“We should do more of this,” Lucifer murmurs against the corner of Sam’s mouth when they break for air. 

“Hell yeah,” Sam mumbles in return.


	13. Date 13:  Deals

Title: Date 13  
Author: Gedry  
Pairings: Anna/Crowley  
Rating: PG - 13  
Word Count: 841  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: none  
Summary: Written for 50 first dates – Deals. 

Date 13

Study abroad.

Anna had thought it sounded like a fabulous idea when she had been approached with it by her professors. 

Study abroad, immerse yourself in a new culture completely, live with an exchange family and let them be a safe place for you to flourish and grow in your skills. 

Learn a new language and learn about life. 

What the fuck was she thinking?

Germany is nice. Okay, it’s not nice it’s god damned gorgeous. The rolling hills and bustling cities, smushed in with tiny towns with amazing food and welcoming people is like the antithesis of Anna’s experience growing up in her very insulated, very narrow minded town. 

The family she was placed with is so kind to her and she loves them for their understanding and patience with her as she struggles to acclimate. 

The problem, the huge horrible problem she has is that they are keeping a second student along with her. One from another country. A boy. 

He’s an asshole.

Crowley. 

Anna’s not even sure if that’s his first name or last name. They don’t talk enough for her to know anything about him other than he’s Scottish and full of himself in a way that makes her stomach churn. 

He picks on her all the time. Every other word he mutters in his accented English is about her red hair or her thin boned body. 

He apparently thinks that she’s an anorexic leprechaun. 

Anna wants to go home. 

“Looking for your pot of gold?” Crowley comments as he finds her sitting in the small garden attached to the back of their temporary home. 

She adds terrible timing to his list of faults. 

“Go away,” she mumbles as she tries to figure out how to wipe the tears off her face without him noticing. Not that it’s possible. Crowley makes it a point to notice everything about her and then throw it right back into her face. 

“You don’t own the place,” he snorts. “Think I’ll stay right here thank you. Now shove over.”

He nudges her side, trying to force her to move to one side of the bench she’s on. She refuses to move. 

“Come one now,” he presses. “Move. You’re making me feel unwelcome.”

“You?!” She shrieks. “I’m making you feel unwelcome?” 

She snaps. She knows it. But she simply can’t call home again. Her older brother, Gabriel, has threatened repeatedly to get on a plane to Germany just to kick Crowley’s ass. If she tells him she let him bully her again he might actually do it. 

Anna can handle this. She can. 

She’s ready for him to snap at her or to call her a baby. But his eyes widen when he sees her tear streaked face. “Why are you crying?” He blurts out while he digs through his pants pockets until he pulls out a handkerchief.

It’s linen, she notices when he hands it to her. Who still carries those?

“Did something bad happen?” He presses.

“You happened you limped dick little fucker!” Anna snarls, she’s channeling her brothers. Gabriel would be so proud. “You and the constant picking on me. What the fuck did I ever do to you?”

“Nothing,” Crowley says softly as he steps forward to take the handkerchief from her and uses it to wipe her face. It’s tender. She hadn’t expected that from him. “There,” he says, sounding all business. “Now that that’s over how about some lunch?”

“You’ve got to be kidding me,” Anna says flatly. 

“Look,” Crowley comments as he tucks his hands back into his pockets. “I’ll make you a deal. You go to lunch with me, I’ll pay and you can listen to me explain to you why I’m not an asshole.”

“And after that?” Anna says suspiciously. 

“Gelato,” Crowley says with a grin. “You love that.”

“No,” she sputters, confused. “Why are you doing this?”

Then he’s touching her cheek gently with just the tips of his fingers before tugging on her hair with this look on his face that seems sort of distant and self depreciating. 

“You’re asking me on a date,” Anna breathes. His eyes snap to her face.

“Would you say yes?” Crowley asks. He’s still holding her hair. 

“I’ll make you a deal,” Anna offers in return. 

“Terms?” He asks. 

“I’ll go to lunch and you can tell me why you’re being such an ass,” Anna explains. “In return you stop picking on me all the time.” 

“Deal,” Crowley nods. “You know, where I come from we seal deals with kisses.”

“Try me again after the gelato,” Anna says with a glare as she goes in to change. “I’m not promising anything.”

When she’s ready she finds him in the garden, running his fingers over the handkerchief still in his hands.


	14. Date 14 Disney

Title: Date 14  
Author: Gedry  
Pairings: Gabriel/John  
Rating: PG - 13  
Word Count: 666  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: I haven’t been to Disney in a LONG time. I’m assuming that the cast members in the suits don’t talk. If I’m wrong I am so sorry.   
Summary: Written for 50 first dates – Disney. 

Date 14

“It’s hot,” John grumbles as they wander around the park.

Gabriel rolls his eyes inside the giant Donald Duck head he’s wearing. They’re in Florida, it’s always hot. Granted the suit he’s wearing is air conditioned but still, John’s wearing a nice shirt and a simple pair of pants. Gabriel’s wearing the full Duck outfit. 

He’s waddling like a two year old with a really dirty diaper. 

He can hardly see and he’s been groped by three grandmothers today already and the shift just started. 

It’s boring as hell too. They have rules. Gabriel’s not allowed to say anything as long as he’s in character and John almost never talks. For Gabriel, the consummate extrovert, it’s almost impossible for him to follow the rules. 

Thankfully the time goes by pretty quickly between the wandering around blind and hugging nine thousand children before lunch time. 

When their break comes Gabriel trails along behind a stern looking John into the back alleyways that lead them to where he can slide out of most of this suit and relax for a bit. 

After taking off the head Gabriel gives a groan of happiness and rolls his head around until his neck pops. When he opens his eyes John’s watching him with his eyes wide and his mouth slightly open. 

John’s sweaty. Maybe it is really hot today. Gabriel hasn’t been paying enough attention to notice. He’s been trying to hard not to trip over his duck feet. 

“You okay?” Gabriel questions as he shakes his arms and goes to wipe the hair back off his face. 

“What?” John jerks like Gabriel slapped him. “Yeah, whatever. Just eat your food.”

Gabriel rolls his eyes. He and John have been partnered up nearly every shift since they both started the season. It’s partly because Gabriel’s obnoxious as crap and he knows it. He loves practical jokes and has pissed off nearly every other helper he’s had. It’s his third year doing this on his college break. 

John’s a first timer, filling in his time between military service and actually settling down in the fall. Through the grape vine Gabriel’s learned John was engaged to his high school sweetheart when he joined he Marines to make a better life for them. He did two tours in Afghanistan and found out half way through the second one that he wasn’t engaged anymore. 

Mary wasn’t cut out for the wife of a Marine. She married the quarterback of their high school football team instead. 

“Look,” John huffs as he helps Gabriel back into the suit after they eat, spending most of lunch joking about the fact that Rufus and Bobby fell in one of the lakes yesterday on their shift. “Do you want to have dinner with me?”

“We have dinner all the time,” Gabriel comments as John starts to put the head on him. “Why are you so nervous?”

“No,” John sighs and finally meets Gabriel’s eyes. “I mean like a date. You and me.”

Gabriel’s about to blurt ‘YES!’ because John is hot and Gabriel wants him all kinds of badly. But before he has a chance to say anything John slams the head on him and Gabriel’s incased in the cone of silence again until after work. 

He grabs his guide’s arm before John has a chance to pull away and presses his bill to John’s cheek

It’s a weird first kiss but Gabriel figures it makes his point pretty clearly. 

John holds his hand until they see the first set of screaming children. Gabriel can’t stop smiling.


	15. Date 15:  Goodnight Kiss

Title: Date 15  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 580  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Good night kiss. 

Date 15

He’s got stubble.

Well duh, he’s a guy. Cas really should have suspected as much but for some reason the physical sensations associated with this much anticipated event haven’t managed to seep into his brain yet. 

Dean Winchester is finally kissing him. 

Finally. 

It’s taken five years of steadfast friendship, a solid three hundred and sixty five days of crushing, and three sweet dates that included everything Castiel could have ever asked for with the exception of a passionate embrace. 

He loves Dean, he’s pretty sure he loves him utterly and completely. Cas wants to spend his life with this young man that befriended him when no one else paid him a moments notice and then opened his heart to him when Cas had though he must surely be wanting more from Dean alone. 

They’ve held hands, curled up together on Dean’s beat to hell sofa watching a movie that Cas will never remember, and now Dean’s leaned toward him, pressing up against the side of the Impala and pinning him with his arms on either side of Cas’ body. 

The approach alone is enough to make him achingly hard. He can tell Dean notices as soon as his thigh brushes Cas’ dick through his pants. Dean’s eyes widen and his cheeks flush pink. Cas pants with nervousness and reaches up to cup along the sides of Dean’s chest hoping that his tough is welcome, wanted. 

And it is. 

Dean groans as his face closes the last of the distance between them. The stubble he hadn’t counted on brushing along his chin and catching against his cheek. Cas gasps, his mouth falling open at the feeling of Dean so close, the scent of leather, and oil, and man that he’s come to crave so much. 

Dean’s never been one to turn down an opportunity, and the next thing Cas knows what he though was going to be a hesitant first press of their mouths together has turned into a white hot flash of Dean’s tongue sliding along his. Dean tangling his hand into Cas’ hair and tipping his head to the side so he has better access and oh….OHHH…it’s so good. It’s hot and perfect and Cas mewls with pleasure when Dean shoves him back against his beloved car and presses his thigh between Cas’ legs to give him some much appreciated friction against his erection. 

Dean’s hard too; thick and firm against Cas’ hip bone and the space between their bodies keeps getting smaller and smaller from where Cas keeps dragging Dean closer and closer to him. 

He’s still not close enough, never going to be close enough and this had better never end. Cas is going to be a puddle of hopeless arousal when this is over and everyone will know. His brothers will sense it on him that everything has changed and he belongs to Dean now. 

There’s this nip of teeth on his bottom lip and it makes him jerk and growl and give back as good as Dean is giving. It’s wet and messy and oh so good. 

So perfect. 

Over, as Dean slides slowly away. 

“Good night Cas,” he whispers.

And God knows, it really is.


	16. Date 16:  Skating

Title: Date 16  
Author: Gedry  
Pairings: Sam/Lucifer  
Rating: PG - 13  
Word Count: 623  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Skating. 

Date 16

Hockey is a way of life. 

A calling. 

It gives our existence on the face of this planet meaning. 

At least that’s what Sam has always been taught to believe. And he did believe it, totally and completely, until he blew out his knee and was told he would never compete again. 

Goodbye Olympics, hello coaching. 

Still, he’s a damn good coach and his team of rough and tough men might just make it to the finals this season. 

Granted, they are in elementary school. 

Sam likes kids. 

Except when he has to share his training space with the ice skaters; the kids aren’t the problem though they are a little snobby sometimes. No, see, the problem has always been their coach. The aloof and uncaring Lucifer Novak who glares at Sam from across the ice like a panther stalking something. 

He gives Sam the creeps. 

“Winchester,” Lucifer announces as he slides to a graceful, elegant, even stop where Sam is setting the goal up. “We still have ten more minutes of our practice time left. You should wait for us to finish before you drag your equipment into our way. Some of my students have a future unlike your rag tag little bunch of heathens.”

Telling the guy to fuck off in front of all these kids would probably get Sam fired. 

“Just because you started late doesn’t mean I have to. Your times up by the wall clock Novak. Now get off the ice,” Sam answers. 

And he does, but for once he doesn’t leave. He stays, hovering outside the ring of ice as Sam drills his kids and then helps them out of their gear and into their shoes before handing them back to their parents. 

“You’re surprisingly effective at what you do,” Lucifer comments as he joins Sam on the ice while Sam gathers up loose helmets and pads from all over the place. 

“I would thank you but I doubt that’s really a compliment,” Sam snorts then hisses as his knee complains at a deep dip he makes to grab at a puck. 

Lucifer doesn’t answer; he turns abruptly and heads toward the entry way back to outside the ring. His back is straight as a nail and Sam considers for a moment that maybe he missed an olive branch here. 

So he skates up beside the other man and turns quickly, covering Lucifer in a fine sheen of ice shavings. 

Sam laughs, it’s ridiculous. Lucifer glares at him with his head cocked before launching himself after Sam with a warning growl and chasing him across the ice. Sam dodges and spins out of the ice skaters way as much as he can. He’s having fun, enjoying himself as they play cat and mouse and from the rumbling chuckle he hears to his left Lucifer is having fun too. 

Then his knee gives out and Sam goes boneless hoping to limit the amount of damage he’ll take when he hits the ground. But he ends up hitting Lucifer instead who holds Sam like he would a partner executing a dip before having him back up and holding Sam’s weight against his side. 

“Don’t hurt yourself,” Lucifer warns. “I don’t want that.”

“What do you want?” Sam whispers as they glide around in an ark under Lucifer’s control. 

“Whatever you’re willing to give me,” Lucifer answers and it’s not a question. 

Sam takes him home and makes him dinner. He lets himself be dessert.


	17. Date 17: Road Trip

Title: Date 17  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 543  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Road Trip. 

Date 17

He’s not sure how many miles they’ve gone today. He’s not sure he really even cares at this point. The road stretches out in front of them like a beacon and there’s nothing behind them but things they’ve done before. 

This is freedom, maybe tinged with a little bit of something he might think about calling love once he works it all out. 

Cas looks good with the sun on his face. He’s leaned back against the seat with his mouth slightly open and his eyes closed. Dean’s let him sleep a little this morning because Cas isn’t a morning person and they were up late as hell last night at that bar. 

Dean’s not sure what he’s going to have to do to get Cas to understand that he’s not interested in sleeping his way through their last big friendship blow out before Cas goes off to college. Or rather maybe Dean is interested in sleeping his way through it but only with Cas. 

These woman in these bars are like the towns they travel through, pretty to look at but Dean doesn’t want to live there. 

Cas looks like a place he could settle down into though. Cas looks like home. 

If Dean can even figure out how to tell him in a way that Cas understands. 

Communicating with his best friend has never exactly been easy. Cas has clueless down to a science and Dean’s always sucked at that class. 

“You’re staring at me,” Cas accuses without even opening his eyes. 

“I’m driving,” Dean defends as he snaps his eyes back onto the road. 

“You’re staring at me and pretending to drive,” Cas comments as he sits up and stretches his body as much as he can in the old car they are traveling in. 

“I think you mean that the other way around,” Dean says with a little finger twirl and Cas shakes his head. 

“No,” he assures Dean. “I said it correctly.”

“Whatever dude,” Dean shrugs as he keeps his eyes suddenly glued to the road. “You want to stop for something to eat?”

“Not yet,” Cas says slowly as though he’s actually thinking hard about it. “Unless you’re hungry and then I could eat.”

Dean rolls his eyes ‘I could eat’ is Cas speak for ‘I am starving right now but I don’t want you to stop unless you feel like it.’

“Dude,” Dean blurts. “Just say you’re hungry. Fuck! Why do you always say one thing and mean another?”

“I’m not the only one who does that Dean,” Cas sighs. 

“Oh yeah,” Dean snorts. “Because I’m complicated enough to do something like that. You’re the brain here.”

“Untrue,” Cas argues. “Once you said to me ‘Let’s go on a road trip before you leave for college,’ and what you really meant was ‘I love you, don’t leave me.”

“You said yes,” Dean mumbles. “What does that mean?”

Cas touches his thigh gently. “It means ‘I love you too and come with me.”

So he does.


	18. Date 18:  Blind Date

Title: Date 18  
Author: Gedry  
Pairings: Gabriel/Dean  
Rating: PG - 13  
Word Count: 622  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Blind Date. 

Date 18

“Why did I let you talk me into this?” Dean hisses into his phone as he walks into the crowded restaurant. 

“Because you’re lonely,” Sam insists. “I don’t care what you say. And because I have good taste.”

“That’s debatable,” Dean snorts. “Your relationship history is ugly with a capital UG.”

“I did a good job picking out Cas for you,” Sam points out. He’s right too, Dean and Cas may not have been a love connection but they are close friends. He can count on Cas. It’s one of the reasons he’s doing this. 

Cas’ brother Gabriel’s new in town and both his brother and his best friend insist that Dean and Gabriel must meet. 

Like it’s going to be some kind of cosmic love connection. 

“I hate you,” Dean grumbles as he scans the restaurant already panicking when he can’t pick out his date in the crowd. 

“Little soon for that,” a voice says from behind him. “People don’t usually hate me until the third date.”

“Gabriel,” Sam says when he hears the voice through the speaker of Dean’s phone. Dean hangs up on his little brother before Sam has a chance to make him look like more of an ass. 

“I didn’t mean you,” Dean explains. “I was talking to my brother.” 

Gabriel’s short. It’s the first thing that pops into Dean’s head. He’s not like, little people tiny, but he’s shorter than Dean and that’s kind of - nice actually. Dean’s used to being the short one pinned in beside Sam most of his life. 

Alright, the guys smile is killer too; open and friendly with just the right touch of mischief that it makes Dean’s mouth curl up into a grin without him really thinking about it. 

“Brothers,” Gabriel huffs dramatically, like he exasperated. “I have a few of those. I get it. Honestly though Sam’s no where near as bad as some of mine.”

Dean laughs, like actually laughs for what feels like the first time in forever. By the time they are seated and halfway through dinner he’s forgotten this is a blind date, by dessert Dean feels like they’ve known each other for years and it’s sort of second nature for him to reach up an wipe a bit of smeared cherry filling off of Gabriel’s lip when he sees it there. 

Dean stumbles to a halt as they exit the restaurant. He’d forgotten they didn’t come together. 

“Thanks for dinner,” Gabriel offers as they both hesitate on the sidewalk. “I wouldn’t mind doing it again sometime…”

“Third date huh?” Dean questions. 

Gabriel looks a little startled. “What?”

“You said most people don’t hate you until the third date,” Dean reminds him. “It’s still early. I don’t think this even counts as a first date since our brothers set us up.”

He sees it the moment Gabriel gets it. There’s this glimmer of mirth in his amber and green eyes. “Well if that’s the case then I think we should start our first date as soon as possible.”

“Would you think I was easy if I invited you back to my place?” Dean asks hesitantly. 

“Absolutely,” Gabriel blurts. “At least I would pray that you were after I said yes.” 

Dean rolls his eyes while he chuckles only to have it abruptly cut off by the wet, warm caress of Gabriel’s mouth against his. 

He tastes like pie and gourmet coffee. 

Dean thinks he can live with it.


	19. Date 19:  Wedding

Title: Date 19  
Author: Gedry  
Pairings: Cas/Dean  
Rating: PG - 13  
Word Count: 597  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Wedding. 

Date 19

“Do I look okay?” Dean asks for the third time as they drive up to the church.

“Dean,” Cas sighs like he’s silently praying for strength. “You look great. The wedding is going to go perfectly and nothing bad is going to happen.”

“I’m going to fuck this up,” Dean hisses as they get out of the car and head toward the chapel. “Oh God,” Dean gasps as he starts searching his pockets. “Where’s the ring? I lost the fucking ring!”

Cas calmly waves it in front of Dean’s face as they walk in the door. “You gave it to me hold onto for you. Remember?”

Dean snatches it from his friend gratefully. “Thanks Cas,” he blurts. “I could kiss you.”

Dean’s dashing away so fast he almost misses it when Cas mumbles: “I wish.”

He’ll think about that later; right now he has to go be a best man. 

*****

“Are you feeling more sane now,” Cas comments as he comes to stand next to Dean at the reception. “Or do I need to go back to the car and drag out the holy water and start chanting in Latin?”

“Very funny,” Dean snorts with a roll of his eyes. “Thanks Cas,” he adds more seriously. “I couldn’t have done it without you.”

“What are best friends for,” Cas says with a shrug before looking away and staring out at the dance floor. 

Dean takes the moment to study the side of his friend’s face. Cas is a good looking guy. Dean’s always known that. Hell, right now he has a trail of bridesmaids following him like baby ducks wherever he goes. Cas could go home with any of those women tonight, but Dean knows his friend. Cas isn’t like that. He’s a good man. He has a good soul. 

A beautiful soul if Dean’s being totally honest with himself. Hell, he’s over thirty, maybe it’s time to put all those things pounded into his skull about being a man’s man to rest. 

Maybe it’s time to try being happy with someone who makes him feel whole. 

“You’re more than that to me and you know it,” Dean snorts as he playfully elbows Cas in the ribs. “You’re like my other half.”

Cas’ eyes snap to his face in a rush. “What did you say?” his friend rumbles low in his throat. 

“You’re like my husband,” Dean says with a wave, hoping like hell he heard Cas right about that kiss. “You know, without the benefits.”

Cas’ shoulders slump. “Yes, indeed. No benefits.”

Dean grins. He can handle this. “I was thinking we should do something about that.”

“About what?” Cas stumbles over the words. 

“The benefits,” Dean prods gently. “You know about adding them in. I figure we would have to start slow because I’m new at all this…but you’d be patient with me right?”

There’s this moment ripe with possibility when Dean feels like his heart is going to bust out of his chest. Then Cas goes from looking dumbfounded to smiling like the cat who ate the canary. “In all the years you’ve known me Dean, when I have ever NOT been patient with you?”

He holds out his hand and Dean follows him, blushing, out onto the dance floor. 

Man, are those bridesmaids going to be pissed.


	20. Date 20:  Baby Animal

Title: Date 20  
Author: Gedry  
Pairings: Cas/Dean  
Rating: PG - 13  
Word Count: 656  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: None  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – baby animal. 

Date 20

The thing about working at the aquarium is that it’s never really boring. 

Peaceful sometimes, tranquil even, if you don’t have Dean’s job. 

Dean takes care of the penguins. 

The loud, demanding, forceful, self-protective penguins and did I mention it’s mating season?

Well it is, which translates into meaning that Dean’s personal love life is reduced to jacking off in the shower for stress relief while desperately trying not to think about the noise that said penguins make all day long every day. 

So yeah, it doesn’t sound like a big ball of laughs but Dean loves it. His little babies follow him around the enclosure like they’re waddling after their giant odd looking momma and he takes a lot of pride in the fact that his little colony is one of the healthiest in the nation. He works hard and it shows. 

So it bothers him when he has to go tricking his first year parents by swapping out the eggs they aren’t incubating right. But the population needs to grow and taking them away from their parents for just that little while will help give these eggs a chance for a healthy start. 

Besides, he puts them back when they are hatched. They won’t know the difference. 

Of course, the new vet is hotter than hell too so that doesn’t exactly help Dean’s level of sexual frustration. Castiel Novak is new to the zoo, Dean’s barely spoken more than five words to him that aren’t directly related to the job and he’s pretty sure those five words were directions to the bathroom. 

The guys good though, he gives Dean’s eggs a solid but careful once over and leaves Dean to do his thing. After all Dean’s the expert here. 

Or eggspert as Gabriel teases him. 

Everything goes down as planned until Dean gets to Zeppelin. “Come on little guy,” he whispers to the egg when it fails to hatch as scheduled. “Don’t do this to me. You can do this.”

“Dean,” Castiel says softly from behind him. “It might be time to let it go.”

“Look,” Dean snaps as he places himself between Novak and the incubator that’s heating Zeppelin up. “I get you have your vet thing. So why don’t you go do that? This is my territory and I haven’t lost a viable egg in three years. Today is NOT the day.”

Dean dismisses the other man then and spends the afternoon humming Led Zeppelin to the egg as the little being inside of it decides if it’s going to live or die. 

He goes to take a break after the day staff goes home. When he comes back Dean’s shocked to find Castiel Novak hunched over the incubator with the door up as he shifts and tugs on Zeppelin for all he’s worth. 

“What the fuck are you doing?” Dean bellows so loud that the trays stacked next to him clatter to the floor. 

“He wasn’t going to hatch on his own,” Castiel says calmly without taking his eyes off the egg. 

“So you decided to dispose of him?” Dean spits as he shoves in next to the vet to peer inside the incubator. 

There’s a baby penguin in there. 

“I thought he needed help,” Castiel offers with a shrug. 

“You cracked his egg,” Dean accuses. 

“I….encouraged him gently,” Castiel corrects. “He is a she by the way.”

“Well, damn,” Dean comments and shivers when Castiel’s hand slides over to brush against the back of his softly. 

“Indeed,” Castiel chuckles before leaning into Dean’s side and sighing when Dean leans back. 

Zeppelin regards them both as if she had it planned the whole time.


	21. Date 21: Medieval Restaurant

Title: Date 21  
Author: Gedry  
Pairings: Sam/Gabriel   
Rating: PG - 13  
Word Count: 599  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – medieval restaurant. 

Date 21

“Where are the utensils?” Sam asks as he stares at the bench in front of them like something magical might happen at any moment. 

“There are none,” Gabriel comments as he digs into the chicken with his bare hands. “You just eat it with your fingers like they did back then.”

“But there’s a reason why they invented silverware,” Sam explains slowly, like he’s talking to a child. 

“So OCD people like you had a chance to act high class?” Gabriel questions with a cock of his head and flippantly raise eyebrow. 

“Fuck you Gabriel,” Sam answers with a roll of his eyes. 

“Not on the first date,” Gabriel teases. “I’m easy, but I’m not THAT easy.”

Sam chuckles. He knows the truth; Gabriel isn’t easy at all. He doesn’t even understand the meaning of the word. 

He shouldn’t complain too much, after all he’s the one that invited Gabriel to this restaurant. In Sam’s defense he didn’t know at the time what exactly he was getting into he just knew it was a new place and supposed to have built in entertainment. He figured it was a safe place to take a male co-worker that’s over ten years your senior who may, or may not be flirting with you for what may, or may not be a date. 

There are horses here. Sam’s only slightly mortified until the people start rolling out for the performance in period clothing and speaking with bad accents. 

“Oh shit,” he mumbles to himself and focuses on his food as the jousting starts. This is going to be horrible, the worst first date in the history of humanity and he’s going to have to look Gabriel in the eye at the office on Monday. He fucked this up so bad. 

Or at least he thinks he did until Gabriel starts cheering and possibly hurling food items at the guy in the black fake armor who is supposed to be the bad guy.

“You know what your problem is Sammy-boy?” Gabriel announces over the cheering of the crowd after the next competition. 

“What?” Sam asks because he’s frankly stunned that Gabriel is having a good time. 

“You take everything too seriously,” Gabriel clarifies as he wipes at the grease on his hands with one of the wet wipes they were provided with the meal. “I can see it now, we’re going to be old together – or wait, I’ll be old and you’ll still be middle aged because I’m fifteen years older than you. Anyway, I’ll be old and you’ll be standing in the bathroom complaining about the additives the nursing home staff is putting in your jello.”

Sam snorts at the mental picture he’s getting from the brief, sarcastic description. “What will you be doing?” 

“I’ll just be lounging,” Gabriel wiggles his eyebrows. “Waiting for the Viagra I spiked your drink with to kick in.”

Sam falls over laughing so hard he thinks a bit of corn might have come out of his nose. Gabriel reaches out to ruffle up his hair with a level of comfortable affection so high that Sam’s leaning happily into him before he knows what he doing. 

When he looks up Gabriel leaning toward him with eyes full of laughter and Sam melts into the kiss with happy abandon. Gabriel’s worth the risks.


	22. Date 22: Japan

Title: Date 22  
Author: Gedry  
Pairings: Bobby/Crowley   
Rating: PG - 13  
Word Count: 826  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Japan. 

*** NOTE: This story was written prior to the tragedy that occurred in Japan. There’s very little specific to Japan in it but I wanted to let everyone know that. Thanks. 

Date 22

“I’m too old for this shit,” Bobby grumbles to himself as he gets off the airplane and makes his way through customs before heading out to find a taxi. 

One month away from retirement; one last collections trip – Bobby’s pretty sure he’s seen and heard it all by this point but when a book of this level of importance hits the street it’s a big damn deal.

It’s all over the papers. This Brit that goes by the name of Crowley happens upon the last original copy of a manuscript for one of the world’s top playwrights while he’s cleaning out his grandmother’s attic. The damn thing is worth millions, maybe billions on the black market and instead he’s willing to consider donating it to the library at the museum with one small catch. 

Bobby Singer has to come and get it. 

How the hell does anyone even know who he is? 

If the weasel of a guy has so much money he could have sent a car to pick Bobby up at the airport. Never mind the fact that the address he gave the taxi driver apparently doesn’t go to a hotel but to an exclusive neighborhood of condos stacked up to the sky. 

Bobby gets out and drags his suitcase with him more because it’s habit than because he thinks he’s staying here. 

No one’s home when he’s let up to the condo. But that magic book that might as well be made out of pixie dust is sitting unattended on the coffee table like it’s nothing special. Bobby almost has a heart attack before he gets himself together enough to check it out and discovers it to be totally authentic. 

“You know your trade well,” an accented voice says from over his shoulder. 

“I should,” Bobby grunts. “I’ve done it so long I’m almost finished.” 

“It seems I had good timing,” the other man answers. He’s younger than Bobby but not a kid, the guy has some life about him, in his eyes. He’s been places and seen things. 

Bobby likes that in his men. It’s a random thought; one he shakes off as soon as he has it. That is NOT what he’s here for. 

It is indeed Crowley, Bobby finds out as they discuss transitioning the book from Crowley’s hands into Bobby’s care. Some time along the line food gets delivered and Bobby has too much sushi and sake to hold his tongue. “Why did you ask for me?” He blurts as he reclines on the other man’s furniture. 

Crowley grins at him. “I saw you perform a lecture once in Britain. You know your craft better than anyone I have ever met, so much passion from a man wearing a trucker hat and plaid shirt. You don’t give interviews, not even after conferences and you don’t speak at them often enough for my tastes. You see, I’m a lover of rare things; books mostly, things I can learn from. I wanted to learn from you but I never had the chance. You’re reclusive and quite frankly a very surly man with a beard.” 

“What does facial hair have to do with any of this?” Bobby demands. 

“I like facial hair,” Crowley shrugs as he slides the book toward Bobby across the solid wood of the table. “Let’s finish this business please? It’s yours; you take it and do with it what you will.”

“You know how much this thing is worth?” Bobby asks. 

“Of course,” Crowley laughs. “One day I might tell you how much money I paid for it on the black market in order to give it to you. But not tonight; a man needs to have some secrets.”

“Not from your grandmother’s attic then,” Bobby comments with a lift of his brow. 

“Not unless my grandmother is a large Hungarian man with bad dental work,” Crowley chuckles. He’s silent for a long time before adding, “How do you like our date so far?”

Bobby sighs. This guy is clearly insane. But he’s interesting and interested and at Bobby’s age he knows an adventure when he sees it. “Too much business,” he answers honestly. “Not enough passion.” 

Crowley’s eyes gleam in the dim light of the room. “So we have a deal then? You get the book and I get you? You’re retiring, you could stay. We could get to know each other more – intimately.” 

“A deal’s not a deal until you seal it,” Bobby grins. 

Crowley’s dragging him up by the collar and smashing their mouths together again and again before he can get a breath. 

Retirement’s looking brighter and brighter by the second, but then so is the rest of the night.


	23. Date 23: Ren Fair

Title: Date 23  
Author: Gedry  
Pairings: Sam/Gabriel   
Rating: PG - 13  
Word Count: 568  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Ren fair. 

Date 23

Gabriel’s supposed to meet him. Sam tugs on his tights self consciously. Why his date wanted to dress up in period clothing Sam will never understand. But he likes Gabriel. He really likes him. 

Come to think of it really Sam doesn’t think he’s ever felt this way about anyone before. He’s always just sort of fallen into relationships. First with Jessica in high school, back when he was all arms and legs and hope; he’d been lost for a while when she left. Sam has a big heart and losing people is a sensitive issue for him. Then Madison during that summer before he left for college, he’d thought she was the one but then things hadn’t worked out and to add insult to injury she’d taken their dog when she moved out. 

Sam doesn’t really want to admit to even dating Ruby. Some things are better left not remembered or spoken of. Dean even calls her ‘She who will not be named.’

So Sam had wandered on his own for a while until a legal aid project he was working on dropped him in beside a short, abrasive, witty, obnoxious, attorney who’s one redeeming quality was that he fought like hell to serve his clients the best way he could. Gabriel loves the law and sees the hope in it, much like Sam does. But he’s realistic, understands the loopholes and unfortunate circumstances of his clients much better than most and Sam had immediately been attracted to that. 

Gabriel the lawyer is inspiring, Gabriel the man so much more than that. 

He makes Sam’s palms sweat and his heart pound in his ears. He says things that make Sam blush pink all over and hide his smile behind his floppy hair. Gabriel’s warm and complicated and Sam feels like he works his ass off for every little bit of personal information that falls from Gabriel’s beautifully crooked lips. 

So he’s pursuing Gabriel in a way he’s never had to do before and it’s awkward and nerve-wracking. Sam sometimes thinks he’s out of his league but Gabriel’s never refused him. 

So when Gabriel suggested the Renaissance fair, Sam had agreed even before he knew Gabriel had a thing for dressing up. The tights are weird but at least his coat is long enough to cover everything – mostly.

Or maybe not, by the way the women are staring at his crotch. 

Sam’s turning to head back to the car when he catches site of an ornately made up jester juggling a few feet away. People are stopping to watch in wonder but the performance isn’t what Sam notices. Under the funny red and green leotard and face paint is Gabriel. 

Gabriel as a jester seems kind of perfect to Sam.

The performance ends and the crowd disperses after clapping happily. Gabriel wanders over only to do a low bow directly in front of Sam. “Took you long enough to notice me,” Gabriel teases. “What were you thinking about so hard?”

Sam swallows, “How wonderful I think you are,” he answers honestly. 

Gabriel smears his make up on Sam’s chin as they kiss.


	24. Date 24:  Bowling

Title: Date 24  
Author: Gedry  
Pairings: Dean/Cas   
Rating: PG - 13  
Word Count: 751  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Bowling. 

Date 24

The funny thing is that Cas isn’t even drunk. 

It would make total sense if he was drunk. Dean’s been stifling laughter in the palm of his hand all night and it just keeps getting worse every single time it’s Cas’ turn to bowl. 

Oh God, the guy sucks at this so bad. But Dean can’t complain about the view that he gets when Cas stumbles and slides up to hurl the ball into the gutter. 

Cas has a really sweet ass and Dean’s kind of hoping he can shift this little get-together of friends into something more exciting; maybe even more permanent. He’s been having some seriously awesome dreams about the way Cas’ body would feel up against his in bed at night all naked and sweaty. 

He just has to figure out if Cas is interested first. But his friend has always been like a blank slate of sexuality. Cas doesn’t date anyone, he never talks about his past relationships and at the age of twenty-nine Dean is pretty damn sure the guy has to have dated SOMEONE before now. 

Hell, for all Dean knows Cas is dating someone and he just never slips up about it. The idea makes Dean’s teeth grind together and his hands clench. 

“You’re up Cas,” Sam chuckles as he struts back from another strike for his team. Dean trips him as he heads back to his seat and Sam shoots him a glare. 

Cas sighs like a man being told to walk the green mile and picks up his ball. 

They lose the game, of course they do. Cas needs those gutter guards they give to kids when they first start to learn. But it gives Dean an opening to make his move so when the rest of the group files out to go home he offers, “You want to stay and practice? I bet I can help you improve your game.”

Cas smiles. “That sounds wonderful.”

Dean spends the next three hours curved around Cas’ back with his arm pressed against his friend’s as they roll balls down toward the pins again and again. Cas smells good, feels good, moves all smooth with an innate sexuality like a big cat. 

“You want some dinner?” Dean asks as they pack up to leave, it’s late but he doesn’t really want the night to end. 

“How about coffee,” Cas counters as he presses in close and slides a hand down the front of Dean’s shirt to brush over the crotch of Dean’s jeans. “At my place in the morning.”

Dean says yes, who wouldn’t?

Three weeks later Dean’s curved into Cas’ side along the plastic seats in the bowling alley as he watches his brother head up for his turn. It’s the first time they’ve been back there since the night they got together. It’s been a great three weeks. Dean spends most of his free time at Cas’ place. They’re making plans for a trip out of town somewhere, just the two of them. 

The warm fuzzy affection Dean’s always felt for Cas throughout their friendship has blossomed into something Dean thinks just might be the beginning of love. He’s not sold on it yet. He’s never been in love before. 

“You turn Cas,” Sam laughs as he flops back into the seat across from Dean. Cas rolls his eyes before kissing Dean on the temple and whispering “I’ll be right back. Don’t go far.” 

Dean swats him on the ass when he goes by. 

Cas bowls a strike. No one believes it. Sam bets him a twenty he can’t do it again. Cas takes his money with a second strike, then a third, and fourth. 

By the end of the night Cas has collected enough money from their disbelieving friends to pay for their vacation. On the way home he turns to Dean and asks, “Would you believe me if I told you I was a fast learner?”

“No,” Dean growls. “You hustled me.”

“Yes,” Cas admits with a nod. “I was interested in you but I wasn’t sure it was mutual until that night. You couldn’t take your eyes off my ass.”

Dean laughs and after moment Cas joins in. 

Yeah, he decides. It’s definitely love.


	25. Date 25:  Making Out

Title: Date 25  
Author: Gedry  
Pairings: Meg/Cas   
Rating: PG - 13  
Word Count: 680  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Making Out. 

Date 25

The car is cramped and the windows are fogged up. They’re parked out in the middle of nowhere and Cas is still wondering how he ended up here. But Meg is soft and demanding in a way that he has to admit he likes. 

Cas has a thing for bossy women if he’s being really honest about it all. He likes Meg; she’s sassy and rude and scares the shit out of him honestly. So when she ordered ‘Drive me home,’ after drama rehearsal tonight he just jumped up, got his keys out of his pocket and headed toward the car. 

He wasn’t expecting the detour or for her to kiss him, tug him closer, grind herself up against him. She feels good, taste a little like bubble gum and if Cas could just get his hands to stop shaking he might be really enjoying this. 

His best friend, Dean would call him a pussy right now. Dean’s got the aura that makes girls flock to him like bees seeking honey. Cas isn’t like that and why is he thinking about Dean right now?

Her lips move from his mouth to his cheek, his ear, his neck and Cas lets his head fall back until it hit the driver’s side window of his beat up piece of crap. The cold glass behind his head shocks him back into awareness just as much as Meg’s hands dropping to the button on his pants. “You don’t have to do that,” Cas blurts, panting and sweating as he drags her hands away. 

“Look,” Meg says with a glare and flip of her hair. “You’ve been watching me every day for like a year Cas. I get that you have this squeaky clean image of the goodie-two-shoes guy but you don’t have to play that card with me here when it’s just the two of us.”

“It’s not an act,” Cas defends sharply as he pushes her a little farther away. 

“Yeah right,” Meg snorts.

“It’s not,” Cas insists. “You’re right. I’ve been watching you. I…like you. You’re interesting and beautiful and I want to get to know you better.”

“I was trying to get to know you better before he shoved me off,” she snaps. 

“Not like that,” Cas sighs in frustration. “Not yet anyway. I want to get to know what you like, what you think about, how to make you happy.”

“You want to date me?” Meg says like he just can’t believe it. “Me? That’s – not going to happen.”

“Why not?” Cas argues. “I’m good enough to make out with but not good enough to hold hands with in public?”

“It’s not like that Cas,” Meg deflates suddenly, crossing her arms and sinking back into the passenger seat. “It’s the opposite. I’m good enough to make out with in private but you wouldn’t want to be seen out in public with me. I have a reputation.”

Cas laughs; it’s a high pitched nervous sound. “Meg,” he manages to get out through his hiccupping chuckles. “Why would I care what people think? People think I’m an idiot, geek, weirdo. If it weren’t for the fact that Dean and I have been friends since we were five I’d be shoved in my locker everyday after lunch. Go out with me Friday night. We can get pizza and I’ll buy.”

“And that’s all you want?” Meg asks like she just doesn’t understand it. 

“If you have a good time I would love a kiss goodnight,” Cas admits even as he blushes. “And I’d really appreciate it if I was the only one you were kissing while we try to figure this out.”

“I can do that,” Meg agrees and her smile is beautiful when she reaches out her hand and tangles their fingers together.


	26. Date 26:  Chocolate Cake

Title: Date 26  
Author: Gedry  
Pairings: Anna/Jo   
Rating: PG - 13  
Word Count: 763  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Chocolate Cake. 

Date 26

“It says we need eggs,” Jo announces from where she’s bent over digging around in the refrigerator. “But I don’t see any in here. We’re going to have to go to the store. I told you this was a bad idea.”

“They’re on the counter,” Anna replies calmly. “The recipe said to let the ingredients reach room temperature.”

Jo backs out of the fridge with a scowl on her face. “You know, we could have used a box mix. He would have never known.”

“I would know,” Anna argues. “I would know and that’s all that matters.”

“Well excuse me little miss culinary,” Jo sing songs. “Trying to impress a boy with baked goods is all well and good if you can bake. For the rest of us, like me, who are hopeless in the kitchen a boxed mix is more than good enough. He’s in a frat. He probably can’t even find the kitchen in his apartment. He wouldn’t be able to tell.”

“What kind of wing woman would I be if I let you go off with poorly executed chocolate cake?” Anna teases as she looks up out of the corner of her eye to peak at her roommate over the top of her magazine.

Jo grins at her. “Thanks Anna, I’m a little bit out of my depth here. Sam’s a good guy. I like him.”

“I know,” Anna agrees with a shrug. “You’re brave for approaching him. It’s hard to tell someone you care about that you like them some times.”

“What about you?” Jo asks as he measures out flour and sugar with an overly careful eye. “What about the mysterious girl that makes your heart go aflutter? When are you going to make your move?”

“Never,” Anna says surely as she puts the magazine down and crosses her arms over her chest. At Jo’s odd look she adds, “It’s complicated. There’s a lot at risk and she’s a good friend of mine. I don’t even think she likes girls. It’s not worth it to me if telling her might ruin our friendship.” She sighs, “No. You need to add the butter to the sugar before you put the flour in.”

“Oh,” Jo says as she grabs for the butter. “Thanks, I was distracted.”

“Well,” Anna chuckles. “You’re blond. You can’t chew gum and walk at the same time much less bake.”

Jo gives Anna the finger with her tongue sticking out. 

“Don’t tempt me,” Anna warns jokingly. “I might take you up on the offer. Once you go ginger you never go back.”

They laugh and by the time the cake is baking in the oven they’ve settled in on the couch to watch a repeat of Amazing Wedding Cakes. Anna loves it, something about the creative potential involved in small business bakeries. Jo rolls her eyes like it’s the most boring thing on the planet but honestly the cakes are kind of interesting. 

Anna walks her through creating homemade icing, it’s amaretto; then leaves Jo to slather it around the cake on her own. By the time she comes back Anna’s changed into soft fleecy pajamas with monkeys all over them. They make Jo smile as she offers “Want a piece?”

Anna’s brow wrinkles up in confusion. “You can’t cut it! You made it for Sam.”

“No I didn’t,” Jo admits with a smile. “I like Sam and everything but he’s not my type. I made it for you. It’s your favorite cake and you never make it for yourself. So have a piece with me, please?”

“Why didn’t you just tell me?” Anna questions as she walks around the counter into the kitchen.

“What better way to show someone you care about them than to shower them with their favorite baked goods?” Jo waves her hand at the cake. “Besides, I was hoping my attempt at baking would show you how interested I am in you.”

“In me?” Anna asks. 

“Have some cake,” Jo whispers as she reaches up to brush the hair back from Anna’s face. “Then maybe you can tell me why you thought I wouldn’t want to be with you too?”

Anna grabs her then, kissing her senseless. Jo thinks she probably smears icing up the back of Anna’s pajamas but neither of them really cares.


	27. Date 27: Morgue

Title: Date 27 Morgue   
Author: Gedry  
Pairings: Dean/Cas   
Rating: PG - 13  
Word Count: 899  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Morgue. This is a prequel. 

Date 27

“So,” Castiel says as he turns the light on over the body. “Tell me a little bit about yourself.”

Of course, there’s no answer. There rarely is when one is talking to the dead. But it’s a habit that he maintains anyway. It’s caused some discord among his colleagues and left Castiel isolated on the midnight shift. But he really doesn’t mind. Though he grew up in a large family, his somber disposition has frequently led to him being on his own. 

He’s comfortable this way. He clicks on the recorder and begin speaking, “The deceased is a white man between the ages of twenty-five and thirty. He has several gunshot wounds to the chest cavity. However, the cause of death has been determined to be suffocation.”

“How did you figure that out?” A voice rings out from behind him. 

Castiel turns with a raised eyebrow to face the man who’s interrupted him. “He told me,” Castiel explains and expects for the young man on the other side of the room to laugh or roll his eyes as the others do. 

“Okay,” then man says instead. “Did he happen to tell you who did it to him?”

He’s walking closer but hovers at the edge of Castiel space around the table, careful not to enter. “Not yet,” Castiel rumbles as he puts the recorder away. “But we’re just beginning our relationship.” 

The young man grins at him, green eyes flashing and Castiel’s shocked at the jolt of arousal he feels in response. For a moment he’s flustered, uncertain. They aren’t feelings he experiences very often and he contemplates taking a step back from the other man. “May I help you?” he manages instead. 

“I’m Dean Winchester,” he smiles as he answers. “I’m working this guy’s case. I just thought I would drop in and see how it was going.”

“Is there a rush?” Castiel asks. He suddenly irritated. “I wasn’t aware there was a rush on this case. If my work is unsatisfactory someone could have simply spoken to my supervisor. They didn’t need to send you here to check up on me.”

“Whoa,” Dean says as he waves his hands. “No one sent me down here. I came on my own and there’s no problem with your work. You’re like a legend actually, you’re never wrong. It’s a little spooky.” 

“I see,” Castiel rumbles. He’s trying to ignore the spooky comment and see the compliment for what it is. “Then what compelled you to come down here?” 

“Two things actually,” Dean shrugs. “My partner and I have a bet going about how this guy died. He says he bled out from the bullet wounds and I say he suffocated. I wanted to know if I was right.”

“You are correct,” Castiel nods. “There was significant blood loss. But he was killed due to the strangling not from the bullets.” 

“Sweet,” Dean positively beams at him and Castiel can’t stop his own smile in return. “Bobby’s going to be so pissed.” 

“You said there was another reason?” Castiel asks. He’s curious, yes, but there’s something about Dean Winchester that makes him want to drag out this conversation and keep him here. Castiel likes him. 

It’s been a very long time since he’s liked someone who was still breathing. 

“Yeah,” Dean squirms. “Um, the second thing was that I saw you testify in the Galligan case last week and you were really impressive.” 

“Thank you,” Castiel says with a nod; that case had been difficult, the defense attorney had worked hard to make him look incompetent. He was proud of his performance. 

Dean nods, “I was wondering if you wanted to have dinner some time.”

Castiel freezes and blinks several times before stammering, “A date?” 

“Sure,” Dean nods again but Castiel sees how hard his hands are clenched. Dean’s nervous…invested in his response. “If you’re into that kind of thing. If not, then no offense.”

“I am not offended,” Castiel is quick to offer the reassurance. 

“Is that a yes?” Dean asks with a soft chuckle. 

“Oh,” Castiel shakes his head. “I’m sorry; I’m not very good at this. Yes, I would enjoy getting to know you better.” 

They have a brief discussion about the details and though Castiel is saddened to discover their schedules often conflict, he’s relieved that Dean seems unfazed about meeting him for dinner the next night while he’s on his break from work. Most people find the morgue uncomfortable but it appears to have little impact on Dean’s enthusiasm. For that, as well as his persistence, Castiel is grateful. 

Dean leaves with a few backward glances and a smile. Castiel waits for the door to shut behind him before he breaks out in a moment of unrestrained excitement and joy that he rarely allows himself to express externally. When he pulls himself back together he turns to the body on the table with a blush and whispers “That will be our little secret, okay?”

If he gives the rest of his notes with a stupid, dopey grin on his face no one here will tell. 

Date 27

“So where did you meet this guy?” Sam asks as he watches Dean struggle into his third shirt of the evening. The other two must have been deemed unsatisfactory as they are now decorating Dean’s room where he’s thrown them to the side. 

“At work,” Dean answers. “I told you that.”

“Yes you did,” Sam says with a slow nod. “But you never said where at work you met him.”

“What difference does it make?” Dean snaps as he glares at himself in the mirror and sighs as he swipes a hand across his face. 

“You’re nervous,” Sam points out. “That’s why I want to know. You haven’t been nervous going on a date since you were twelve and Marcie Troller promised to let you see what was under her panties.”

That gets a smile from Dean and Sam’s shoulders droop in relief. At least he got a reaction that didn’t involve Dean taking his shirt off again. “So spill!” Sam orders with a wave of his arms. 

“I met him on a case,” Dean explains. “So I can’t say too much about it.” 

Sam understands, working as a police detective with a brother who works at the public defenders office has been a dance they’ve learned to do over time. It’s getting easier and they both have a rule about talking about work at home. But this is different, this isn’t work, this is a date; the first date Dean’s gone on since he broke up with Lisa like three months ago. 

“So give me the cliff notes version,” Sam presses. 

“There was body,” Dean mumbles. “I had to go look at it. The guy doing the autopsy was hot so I asked him out.”

“You’re going out to dinner with the medical examiner?” Sam asks. 

When Dean nods Sam rolls his eyes and blurts, “But Dean, Castiel Novak is one weird son of a bitch.”

That gets him the glare of death from his older brother and Sam shrinks back against the door frame. 

“Don’t talk about him like that,” Dean orders. “He’s different. I get that. But you shut your mouth about him. He’s a good guy.”

“He talks to dead people Dean,” Sam argues. “He says they talk back.”

“He means he gets clues from the physical evidence he finds on them,” Dean explains. “He doesn’t mean they actually talk.”

“You sure?” Sam asks. 

“Nope,” Dean says with a grin as he smooths out his shirt. “But I’m looking forward to finding out.”

“Oh God,” Sam groans. “Tell me you’re at least taking him some place nice for dinner.”

Dean blushes. “We both work weird hours. We don’t have a night off together for two weeks.”

“You are NOT going to take him dinner and have your first date in the morgue!” Sam exclaims. 

He watches Dean smile as he grabs for his keys. “Okay, tell yourself whatever you want if it makes you feel better. I’m going out. Don’t wait up.”

After Dean leaves Sam puts a pillow over his face and screams. 

Date 27 – The Sequel

“You look very nice,” Castiel announces by way of greeting when Dean hauls the boxes of Chinese in through the morgue’s doorway. 

“You look very….,” Dean has to think about it for a minute. “Relaxed?” 

Though, that is entirely not the right word at all. Castiel looks about as relaxed as body experiencing rigor mortis. 

The other man looks down as his jeans and t-shirt nervously before shrugging and replying, “I thought perhaps you might be more comfortable in this odd setting if I dressed more casual.” Castiel sighs, “I’m sorry. I’m afraid I’m not very good at this.”

“Dating?” Dean asks as he sets down their food on the desk in corner. 

“The living in general,” Castiel responds and though Dean snorts with laughter when he turns his head back to the other man it’s obvious Castiel isn’t kidding. 

Dean sobers immediately. “Honestly,” he offers before pulling out the computer chair and motioning for Castiel to sit. “I don’t think I am either.”

Castiel smiles at him softly and Dean takes a deep breath. It was obviously the right thing to say. Once they get seated Castiel spreads out the food and Dean sits back across the desk from him watching the confident and delicate way he handles his chopsticks. 

“I’ve always been hopeless with those,” Dean blurts and then blushes. 

Castiel blinks at him from behind his wire rimmed glasses. “They’re simple in theory. The correct application takes practice. I could show you…but you’re sitting too far away.”

Dean raises an eyebrow. “Are you flirting with me?”

“Badly, yes,” Castiel chuckles. “But that is the purpose of a…date, correct?”

Dean laughs as he gets to his feet and shifts his chair around the desk until they’re sitting close next to one another. Castiel removes the paper cover from the second set of chopsticks and pulls them apart before motioning for Dean to take them and mimic what Castiel is doing with his. 

It’s a mess. Dean tries clicking them together in the air like the other man is showing him but nothing seems to want to work together. 

“Like this,” Castiel says gently as he puts his chopsticks down to re-position Dean’s. Their hands brush as Castiel moves and he whispers, “You’re so warm.” 

Dean watches Castiel’s fingertips trail across the skin of his hand in a way that clearly has nothing to do with their food. “Yeah, it’s probably because I’m not dead.”

The gentle petting motion stops immediately and Castiel jerks his hand away. Dean regrets saying anything. 

“My apologies,” Castiel comments as he turns back to his food. “I’m afraid I’m out of my depth here.” 

Dean opens his mouth to reply, but if he’s being honest, he’s just as lost about this as Castiel is. He’s not used to dating; a few drinks a fun roll in the sheets he’s used to having, but this is…bigger than that. 

Instead he leans forward and presses his lips to the side of Castiel’s cheek near his glasses before nuzzling the other man gently. It’s intimate and really outside of his comfort zone to be so physical with someone he barely knows in a non-sexual way. But Dean relaxes as soon as Castiel makes this pleased sounding humming noise in the back of his throat and leans further into his personal space. 

Dean pulls back and they share a smile. It’s easier after that. They eat and chit-chat about work and families. Dean’s pretty sure he’s arrested Castiel’s older brother at some point. It’s hard to forget a loud-mouthed guy named Gabriel. 

He decides not to mention that particular detail. The date’s going too well for that. 

They finish their food with good conversation and then Dean’s struck dumb by the message on his fortune cookie. 

-Your future is looking back at you.-

When he looks up Castiel’s watching him curiously. “Anything interesting?” 

“Nah,” Dean shrugs but he folds it up and stuffs the fortune in his pocket just the same. “What’s yours say?”

Castiel holds it up for Dean to read. 

-A life without risk is a life without living-

“That’s deep,” Dean comments. 

“I suppose,” Castiel says as he turns the paper over and around in his hands. 

Dean watches him for a moment before Castiel sighs like he’s thinking of something horribly unpleasant and announces, “My lunch break is ending in five minutes. I’m sorry we don’t have more time together.” 

“Me too,” Dean agrees. “Want to do this again sometime?” 

“I’m off on Tuesday,” Castiel blurts almost as soon as Dean finishes asking the question. “Please tell me you’re off on Tuesday.”

“I’m off on Tuesday,” Dean assures him. “I work Monday night though so I might be a little sleepy.”

“I do as well,” Castiel nods. “We can plan to meet in the afternoon.” 

“Or I could drive you home from work Tuesday morning and we can spend the whole day together,” Dean offers as he reaches out to trace along the back of Castiel’s hand. 

There’s a pause and then, “I’m not interested in a one night stand,” Castiel states firmly. 

“Neither am I,” Dean says softly while he rubs his hand further up Castiel’s arm. “I just want as much time with you as I can get, even if we’re sleeping. I promise to keep my clothes on and my hands above the belt line.”

Castiel’s lips quirk in a grin. “Alright. I would like that.”

He walks Dean to the door of the morgue, pressed up tight against Dean’s side like he’s starving for warmth and affection. Maybe he is, maybe they both are.

This is the lightest Dean’s felt in years. 

They don’t kiss in so much as Castiel suddenly presses his nose against Dean’s neck and inhales like he’s trying to memorize Dean’s scent. Then he steps away with a blush and the softest brush of fingers against Dean’s cheek. 

It feels more intimate than kissing, so much so it makes Dean’s toes curl.   
He spends a long time sitting in his car outside of the morgue with one hand pressed against the spot on his neck that Castiel’s lips brushed when they were saying goodbye. 

His other hand holds his fortune. 

Dean’s never thought much about having a future….until now. 

Date 27 – The Sequel Part 2

“This is my place,” Castiel says quietly as Dean follows him into his apartment. 

“It’s nice,” Dean comments as he looks around with his hands stuffed in his pockets. “Cozy.”

He might be misreading him but Dean’s pretty sure Castiel is pleased. He’s hard to get a grip on emotionally. Castiel’s moods shift into one another softly, quietly. Dean’s so much more reactive. He wonders if Castiel feels as out of depth with him as Dean does the other way around. 

His thoughts are interrupted by his own yawn. 

“I’m sorry,” Dean offers as he blinks his eyes. “It was a rough shift and I’m really tired.”

“Come with me then,” Castiel says with a nod before turning down a hallway leading to a smaller room off the living area. There are heavy curtains over the windows and a towel shoved behind the door. All the signs of a man who works the night shift. Dean’s room looks almost exactly the same. 

The bed is a king. Dean’s a little surprised. Castiel seems to follow his train of thought because the other man shrugs and offers, “I don’t like feeling cramped.”

“It’s great,” Dean smiles. “I might never want to leave.” 

Castiel doesn’t respond verbally to his comment but the look he gives Dean, smoldering hot with an undercurrent of something that looks like fear, says it all. 

“I’m going to change,” Castiel says as he turns toward the bathroom with a pile of clothing he scoops up off the end of the bed. “You can do the same in here, if you like.” 

Dean doesn’t move until the door to the bathroom shuts behind Castiel’s back. Then he slips his bag off his shoulder and strips off his shirt. He sits on the end of the bed to unlace his shoes. Dean doesn’t usually sleep in anything but his boxers but he has a pair of worn out pajama pants that Sam gave him for Christmas years ago that he slips on with a t-shirt before looking around at the pictures hung haphazardly on the walls. 

There’s one of Castiel, rumpled and dirty, looking sort of wet in running clothing as he stands next to another man. There’s a vague family resemblance in their faces. It occurs to Dean that yes, he really has arrested Castiel’s brother and that he’s fairly certain Sam was his defense attorney. 

He got off too. Sam had rubbed that in so hard! 

The sheets are soft, worn. Dean takes an extra moment to consider that most of Castiel’s things are this way. He’s a man that takes care of what he loves. 

Dean’s pretty sure it must be nice to be taken care of. He’s spent his life taking care of other people. It’s never really been the other way around. 

Castiel comes out of the bathroom a few minutes later wearing a wife-beater and flannel pants hung low off his hips. Dean takes a turn in the bathroom, brushing his teeth putting on extra deodorant just in case. 

Hen he comes back out Castiel is turning back the covers and the lights in the room have been turned off with the exception of a lamp on the bedside table. He swallows, his body frozen and rigid as Dean comes close to his side. 

“Kiss me goodnight,” Dean whispers into his ear and Castiel turns, throwing his arms around Dean’s neck and claiming his mouth with a passion that Dean just knew was there under the surface. It’s hot and wet, just like Dean likes it. Castiel’s stubble rubs over his chin while their tongues dance together and he fists his hands in the back of Dean’s t-shirt trying to tug him closer still. 

Dean drags his body flush up against his and Castiel groans low and deep before pressing tight to him. Dean’s halfway to hard from just the kiss alone when they slowly ease back and blink at each other. 

“Do you have a side preference?” Castiel asks. 

The gears in Dean’s brain grind to a halt at the implication of what the other man might be meaning. “Um…what?”

“Of the bed,” Castiel clarifies, pointing down at the mattress. “What did you think I was talking about?”

“Nothing!” Dean hurriedly blurts as he blushes. But then the corner of Castiel’s lips twitch and he points, “Oh, so you do have a sense of humor.” 

“A good one in fact,” Castiel chuckles. “Most people don’t stay long enough to discover such things about me.” 

It makes Dean’s chest hurt a little. Hell, he just got here and he already never wants to leave. “So, sleep?” he offers instead. He just doesn’t know how to tell Castiel he thinks he’s falling in love when they’ve only had one date together. The guy will think he’s lost his mind. 

Castiel nods and they slip in the bed, both scooting toward the middle until Dean finds himself settling with the other man’s head pillowed on his chest with Castiel’s leg thrown over his thigh. 

It feels so much better than he imagined. 

He reaches out to turn off the light before curling his arm over Castiel’s shoulder and closing his eyes. He’s comfortable, warm, safe, happy, content even. 

Into the darkness of the room Castiel murmurs, “I think I could love you.” 

Dean’s heart skips a beat. This is usually when he grabs his shit and runs like the coward he knows he is in relationships. It’s too much, too soon. 

“Glad I’m not the only one,” he answers instead. 

Castiel sighs and pets along his side with his hand. Dean smiles as he closes his eyes and drifts off to sleep.


	28. Date 28: Row Boat

Title: Date 28  
Author: Gedry  
Pairings: Lucifer/Sam   
Rating: PG - 13  
Word Count: 602  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – rowboat. 

Date 28

“How long have you been working on this thing?” Sam asks as he crouches down in the barn behind the Novak house to peer at the mass of wood and equipment that his friend swears will eventually be a boat. 

“Four months,” Lucifer responds with a tinge of frustration in his tone. “Off and on.”

“Mostly off it looks like,” Sam teases and then smirks at the evil glare Lucifer shoots at him. “Glare all you want, you don’t scare me.”

“Why is that exactly?” Lucifer asks. “People usually find me off-putting but you never have.”

“I like a challenge,” Sam comments as he traces the curve of the wood around the frame with the tips of his fingers. “You know, this is all very NCIS of you, building a boat in your barn. I like it. Should I call you Jethro?”

“I will kill you,” Lucifer threatens. “They will never find your body.”

“Won’t matter,” Sam shrugs. “Dean wouldn’t call the police. He would just end you without the expense of a trial and imprisonment.”

“Your brother is disturbing,” Lucifer shivers as he says it. 

“Look who’s talking,” Sam snorts. “You got a whole house full of crazy going on back there. How many kids did your parents have anyway?”

“Too many,” Lucifer huffs. “Way too many.”

They laugh and Sam wanders his way around the structure until he’s standing close to Lucifer’s side. “Is this what you brought me out here to show me? Your boat?”

“Maybe I brought you out here to kiss you,” Lucifer murmurs as he watches the movement of Sam’s hand while it caresses the grain of the wood. 

“Why aren’t you kissing me then?” Sam asks as he steps closer. 

“You’re teasing me,” Lucifer shrugs. “That and I’m not exactly sure what’s going on between us.”

“We’re dating,” Sam explains softly as he reaches out with his other hand to rub his thumb across the arch of one of Lucifer’s eyebrows. “At least that’s what I thought this was. This is a date right? You don’t just bring all the guys out to the barn to look at your boat frame before they tease you and you threaten to off them, do you?”

Lucifer’s smile is blinding and his hands are warm as he reaches out to slide them along Sam’s sides and around to the small of his back as he tugs Sam closer to his body. Sam’s taller than Lucifer; Sam’s taller than everyone really. But something about the way Lucifer holds himself makes him seem like they are on even ground even this close. 

Their noses bump then rub against each other with lazy affection. Sam relaxes into the embrace and angles his head as he leans over just enough to brush their lips together with ease. It’s easy, kissing Lucifer. Sam had thought this was going to be a complicated dance between the two of them but it’s not. They’re both giving instead of taking and that makes it warm and sweet instead of difficult. 

“Where do you put the motor when you’re done?” Sam asks after several more kisses. 

“It’s a row boat,” Lucifer comments as he nuzzles at Sam’s ear. 

“A row boat?” Sam sputters. “Who uses a row boat?”

“You did say you liked a challenge,” Lucifer smiles against Sam’s neck. 

Touché.


	29. Date 29:  Pet Shop

Title: Date 29  
Author: Gedry  
Pairings: Cas/Dean   
Rating: PG - 13  
Word Count: 590  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Pet shop. 

Date 29

So he’s been trying to work up the nerve to ask Cas out for weeks now. It’s not something Dean usually struggles with. He doesn’t second guess himself a lot in life. If he wants something he grabs onto it and just refuses to let go. 

That’s kind of how they became friends in the first place. But they were kids then and okay, if he’s being honest Dean knows they’re still kids. He just got his driver’s license six months ago and he’s coming down off of his three month whirl wind of dating anything with legs. 

Having a car, even a beat up piece of shit like the one he has, makes it easier to get around. But at the end of the day it’s been hollow. Dean spent a late Friday night slumped on Cas’ bed watching some stupid old Sci-Fi show with him when they both should have been sleeping. It kind of hit him the next morning when he woke up still in Cas’ bed with his friend snuggled up to his side. 

He’d had a better time there with Cas than he had with anyone else in a long time. That and Cas looks really kissable when he’s sleeping. 

Dean had gotten grounded for being out all night so this is the first time they’ve had a chance to spend any time together. 

How they ended up in the pet shop he will never really know. 

“Are you looking for anything in particular?” the woman behind the counter asks. 

Dean shakes his head and grins when his much more polite friend answers with “No thank you. We’re just looking.” 

Cas is always so damned nice. 

They wander around looking at the fish and pointing at the gerbils. The little fuzzy guys are kind of cute really even though Dean hates to admit it. 

“You want to get some lunch after this?” Dean offers stiffly. “I’ll buy.”

If he pays that makes it a date right? Technically he just asked Cas out. He can do this. 

“I would like that,” Cas agrees. But he sounds distracted so Dean turns his head to see his friend staring into a giant cage where a huge-ass white bird is sitting on a branch. 

Dean hates birds. They give him the creeps. 

“He’s impressive,” Cas says as Dean swallows and creeps closer to his side. The bird turns to look at him and it looks too smart for its own good. 

“I guess,” Dean mumbles. He turns around looking for something else to occupy his time while Cas communes with his new friend. 

“The cage says he belonged to an elderly woman who can’t take care of him anymore. That’s sad…oh wait! He lives with the shop owner. Good, he has a home and someone to love him. That’s important,” Cas sounds pleased and it makes Dean smile. 

“That’s what I like about you Cas,” Dean chuckles. “You’re kind hearted.”

“SHUT UP AND KISS HIM!” The bird squawks, making Dean jump. “SHUT UP AND KISS HIM!”

He turns back around to stare that the bird. 

“Well,” Cas comments as he crosses his arms. “You heard him. Shut up and kiss me.”

So Dean does. What’s he going to do? Argue with a bird?


	30. Date 30:  Halloween

Title: Date 30  
Author: Gedry  
Pairings: Gabriel/Dean   
Rating: PG - 13  
Word Count: 715  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Halloween. 

Date 30

The door bell rings for the fiftieth time and Dean sighs as he grabs the bowl of individually wrapped candies and goes to hand them out to the mess of little and sometimes too big children crowded around the doorway. 

“I can’t believe this is what you wanted to do tonight,” he grumbles at Gabriel as he passes the kitchen. 

“Shut up,” Gabriel comments with smile. “You love Halloween and we both know it.”

“What’s your point?” Dean snaps back but he’s chuckling as he answers the door. Gabriel’s right. He loves the whole cyclical awesomeness of this holiday. When he was kid he spent every October thirty first patrolling this same neighborhood for candy from the people who lived here then. It’s only fair that he be the one to give out the best candy to the new kids taking his place now. 

It makes sense to Dean, it fits into that little area inside his heart where the world is still fair and life is still full of the excitement and adventure of his youth. 

Not that he’s old or anything, but at thirty you start to notice that these kids are looking younger and smaller every year. 

It’s nice to have someone to spend it with this year. Sam’s over at Jessica’s place tonight and Cas had to work a double shift at the hospital. So Dean’s feeling pretty good that his best friend’s older brother came to hang out anyway. It’s not often he gets time alone with Gabriel Novak. It’s something he wants more of. 

“Hey Dean,” Gabriel says as he joins him at the door. “We’ve seen that little boy before.”

Dean looks where Gabriel is pointing and notices a little kid, no more than six maybe dressed up like spiderman. He’s walking down the street aimlessly, tears streaking his face. “I’ll be right back,” Dean mumbles before shoving the bowl he’s holding at Gabriel and stalking out into the busy street to catch the kid’s eye. 

“Hey Spidey,” he calls. “Where’s your Ironman gone off to?”

“I lost him,” the little boy whimpers before breaking down in front of Dean who scoops him up and starts a search for his family. 

It doesn’t take long. Gabriel calls him on the cell as soon as he’s around the corner to tell him a lady dressed up like Cleopatra is dragging a tiny Ironman around the neighborhood frantically. 

Dean hands the kid back to his group and strolls his way home through the milling crowd. It’s kind of bittersweet actually; Dean had always assumed that one day he’d be the one walking his kid around to get candy. That’s not really looking like it’s in the cards for him right now. 

“My hero,” Gabriel singsongs when Dean makes it back to the house and laughs when Dean literally kicks him in the ass. 

They have dinner, homemade pizza, and Gabriel being a chef will never stop being awesome. By the time they finish eating the crowds are gone and they’re left to slump on the couch side by side and relax. 

“You should have a dozen kids,” Gabriel comments suddenly. “You were so good with that poor little guy tonight.”

“Yeah,” Dean shrugs. “Not thinking I’m going to get the chance for that this time around Gabriel.”

“We could adopt,” Gabriel replies with a grin. “I mean we should probably go out a few times first. I don’t want you thinking I’m easy or anything. But eventually…we could. I like kids.” 

“Cas isn’t working late is he?” Dean asks. 

“Nope,” Gabriel admits. “He’s at my place with Balthazar. That and I told Sam to go hang out with Jessica. I wanted you all to myself.”

“Tricky,” Dean snorts. “You always were sneaky.”

“How often does a couple’s favorite holiday fall on their first date?” Gabriel asks. “I couldn’t pass it up.”

Dean rolls his eyes, but when Gabriel’s fingers slide up against his he makes a point to hold on as tightly as he can.


	31. Date 31: Abandoned Kittens

Title: Date 31  
Author: Gedry  
Pairings: Gabriel/Dean   
Rating: PG - 13  
Word Count: 834  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None   
Summary: Written for 50 first dates – Abandoned Kittens. 

Date 31

Dean’s seen him around the neighborhood for a while now. Not that he’s stalking the guy or anything. 

He’s not. 

It’s not like that.

He’s just….interesting. Dean’s used to being the only over thirty freak in the suburb that still lives with his equally freaky brother. But then they moved in down the street and now Dean and Sam aren’t oddities on their own anymore. They’re part of a pair. 

The Novak boys, that’s what Mrs. Parsons called them when Dean asked her who they were. Dean’s protective of his elderly neighbors. He and Sam grew up on this street. No nut-job weirdo is going to roll in here and disrupt the peace and quiet. They’re kind of the neighborhood watch enforcement team. 

Sam’s as big as a building unto himself and Dean’s as mean as a junkyard dog. 

But the Novak’s are respectful, quiet. They stick to themselves most of the time and when seen on the street they’re polite but they don’t linger. 

Dean’s sort of sad about the lingering thing. 

Which is why he’s surprised when he’s driving home one rainy night after his late shift at the auto body shop to see the object of his attention huddled over, rain-soaked, in the ditch in front of the McTaverty’s house. 

“Are you okay?” Dean shouts out of his window when he pulls the car to a stop. 

The other guy’s head jerks up and he shrugs while he answers “Not so much. It’s wet out here.” 

“Yeah,” Dean agrees. “What are you doing out here in the rain?”

“They’re stuck.” The other guy answers. “I can’t leave them.”

Okay…that’s a little weird. Weird enough that Dean puts the Impala in park and gets out of his nice toasty car to crawl into a ditch next to guy who he knows nothing about. “Who’s stuck?”

“Look,” the guy points. As Dean bends over and peers into the drainage culvert he sees them; two itty-bitty kittens crowded against the wall of the pipe next to the mess of fencing and wire that the McTaverty’s have put in to keep leaves from blocking the flow of water and flooding the driveway. 

“How did they get in there?” Dean gasps. 

“No idea,” his neighbor replies. “I was getting the mail and heard them crying. I kind of have a soft spot for strays. But then I couldn’t get them out and the water keeps rising. I’ve been trying to pull the metal out of the way but it won’t move.”

“No,” Dean comments with no small amount of chagrin. “It’s not going to budge. I put it in for them. I should know.”

“Oh,” the other says sadly. 

Dean notices he’s shivering slightly and it’s not just the kittens he’s worried about getting out of the cold suddenly. “I’m going to drive my car home. I’ve got metal cutters in my garage. I’ll be right back.”

Dean rushes through the house, grabbing towels, pliers, a hack saw, anything he can find to help pry the kittens free. By the time he gets back to the ditch the water’s raised even higher and his neighbor’s shaking is less of a shiver and more of a full-body shudder. 

It only takes him about eight minutes to cut the cats free and lift them out of the pipe. He’ll come back when it dries up and clean up the mess, repair the damage. 

He tucks the other man and the two cats into the passenger seat of his car and for some reason drives them to his house instead of just pulling into the driveway where he knows the Novak’s live. 

“Gabriel,” the other man says suddenly as his teeth chatter. 

“Huh?” Dean asks. “Weird-ass name for a cat.”

He has a nice laugh; Dean thinks when the guy falls over giggling. “No,” he gasps. “That’s me. I’m Gabriel.”

“Oh!” Dean snorts as he blushes. “I’m Dean.”

“I know,” Gabriel comments. Dean looks at him for a minute, all huddled under towels looking like a drowned rat with two little kitten’s curled up against his stomach. 

Gabriel’s beautiful. 

“Come in,” Dean offers. “I’ve got homemade soup and I’ll start a fire. You can wear some of my clothes until you’re dry and we’ll figure out what to do about the cats.”

Hours later, Gabriel’s still in Dean’s pajama pants and asleep on his sofa in front of his fire place with his head pressed up against the side of Dean’s thigh like it belongs there. One of the kittens mewls as he climbs into Dean’s lap. 

“I don’t know how you guys got into that pipe,” Dean whispers to the kitten as it paws at his face. “But, good job.”

Date 31 Follow Up

It’s the claws digging into his foot from outside the covers that wakes Dean up. 

Same thing, every morning. 

“Lucifer!” Dean complains as he shakes his foot, trying to kick the cat gnawing on his big toe off the bed. “Every fucking morning, cat!”

He wonders sometimes why he let Gabriel talk him into keeping these rotten, spoiled things. 

But just when his annoyance level reaches critical he rolls over to go back to sleep and feels a warm ball of fluff snuggle against his armpit. 

“Morning, Kali,” Dean mumbles absently as she starts a deep, rumbling purr that has always been totally inconsistent to her sleek, tiny, black frame. 

She’s a cuddler, making contended biscuits into Dean’s worn out t-shirt softly enough that he doesn’t even really feel her claws. 

Dean has another half hour before the alarm goes off. He’s not sure how Lucifer knows the time but the cat has radar and attacks Dean’s feet every morning the same way. The only time it varies is when Gabriel sleeps over. 

Not that Gabriel sleeps over that often. 

It’s something that’s kind of a sore spot for Dean. He’d like for Gabriel to stay over more often. 

But things are…complicated. Dean’s withdrawn, Gabriel’s too pushy. They fight; sometimes don’t speak to each other for a couple of days. They aren’t really together, so they can’t break up. Not that Dean would want to break up with Gabriel…if they were together.  
But they aren’t. 

Dean groans and rolls out of bed before his alarm goes off after dropping a kiss to Kali’s furry face before tripping over Lucifer who grabs for his ankle the second his feet hit the floor. 

He grumbles on his way to the bathroom but detours to the kitchen to pour food into the cats bowl first. 

Lucifer meows at him appreciatively. “Yeah,” Dean bitches. “I’m so fucking well trained.” 

He’s done with his shower before he remembers he forgot to start the coffee when he was in the kitchen. “Fuck my life,” Dean sighs. 

Gabriel’s waiting for him in the living room with a fresh, hot cup. 

“I love you,” Dean blurts out as he grabs for the coffee. 

He’s drinking it down and burning his tongue before he realizes what just came out of his un-caffeinated mouth. 

“Good morning to you, too,” Gabriel says by way of answer. Dean’s still floundering for a response when the smaller man gets to his feet and presses up against his side to nuzzle the side of his neck. 

It’s the pinch on his ass that finally makes Dean suck air back into his lungs. “Giving you a key was a really good idea.”

“You’re only saying that now because I came with coffee,” Gabriel chuckles as he steps away. 

“Maybe,” Dean nods before draining the cup and setting it down on the table next to the couch. “Maybe I should try saying nice things to you more often.” 

“Are you sick?” Gabriel snorts. “It’s not really our style.” 

Dean reaches out to grab Gabriel’s arm when the other man goes to step toward the door. “Are you happy?”

“Like in general?” Gabriel asks while he looks at Dean like he’s loosing his mind. 

“With me specifically,” Dean exhales slowly. Sometimes talking to Gabriel is enough to make him want to scream. They’re both so independent. 

“With you?” Gabriel repeats dumbly. 

“Yes, damn it!” Dean huffs. “With me, as in ‘us’, you know…us!”

“Is there officially an ‘us’ now?” Gabriel shoots back as he crosses his arms. 

“You have a key to my house,” Dean points out. 

“When you gave it to me you told me not to read anything into it,” Gabriel huffs. 

“We have pets together,” Dean argues. 

“You have physical custody and I get visitation,” Gabriel comments with a shrug. 

“Jesus,” Dean throws up his hands. “I give up, you know. I’m standing here, telling you I love you and you acting like this is a huge joke. I’m tired, Gabriel. That fucking cat jumps on my feet every morning except when you sleep over and this morning after I shook him off I was thinking about it and about you and I want more than this weird…thing we have.”

“I thought you just really loved the coffee,” Gabriel offers after a long pause with a smile that never makes it to his eyes. 

Dean bites the inside of his lip as he turns to head back to his bedroom, throw on his work clothes, and stop making an ass of himself. 

This is why he’s never had a real relationship…so fucking complicated. 

But he has to give it to Gabriel; the guy is right behind him. 

“So you want things to be different,” Gabriel blurts as he shifts his weight from one foot to the other. “Like how?”

“You want terms and conditions?” Dean challenges. He’s ready to call in sick, crawl back into bed and pray this has all been a horrible dream by this point. 

“I don’t know!” Gabriel exclaims throwing up his arms. “I suck at this. This is as committed as I have ever been to anyone. Hell, we basically have kids together. I want to be here all the time but you never ask me for anything, Dean! I don’t know what to do!”

“Stay,” Dean says simply. “I want you to stay.” 

The next morning, Dean wakes up to Gabriel pressing his freeze toes against his foot under the covers and wonders if the damned cat might not have been the better choice. But then Gabriel whispers, “I love you, too.” 

And hey, Dean’s got a half hour before the alarm goes off…they might as well make the most of it.


	32. Date 32: Merry-Go-Round

Title: Date 32  
Author: Gedry  
Pairings: Gabriel/Castiel   
Rating: PG - 13  
Word Count: 673  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: It’s two brothers on a date – sort of.   
Summary: Written for 50 first dates – Merry-go round. 

Date 32

“Remember when we used to do this when we were kids?” Gabriel asks as he spins the metal circle they are sitting on in the park around slowly with his foot. 

Cas sighs as he hangs onto the bar and watches the world rotate around him. The world spins a little bit and he can’t help but feel a bit disconnected from everything around them.

It’s been a rough day. The funeral and a wake filled with relatives they almost never see or have even heard of is wearing Cas out. 

“Why did you leave?” he asks. The merry-go-round slides to an abrupt stop as Gabriel puts his foot down hard onto the ground. 

“It’s personal,” Gabriel murmurs. 

“I’m your brother,” Cas argues. 

“I know,” Gabriel snaps. Then adds more softly, “Believe me...I know.”

“I have a right,” Cas presses as he squeezes and grips the metal under his fingers more tightly. “I have a right to know why you left me here and never came back.”

“It was years ago,” Gabriel says as though that makes a difference. “I wanted you to be happy.”

“What did my being happy have to do with you being gone?” Cas snaps. “How was my brother abandoning me supposed to make me happy?”

“I don’t know what to say little bro,” Gabriel sighs. 

“Our father’s dead,” Cas murmurs as he kicks the merry-go-round moving again and the world blurs away. “You’re going to fly out tomorrow and I’ll be alone. Thanks for making me so happy.”

Gabriel makes a noise that sounds like a small animal, scared and maybe hurting. “I didn’t want this.”

“Then what did you want?” Cas bellows. “What do you want that is so terrible you’d rather run than touch me?”

“You!” Gabriel hisses through clenched teeth. “I want you. I’ve always wanted you and it’s wrong and now you’re going to hate me.” 

Gabriel slams his foot down again. The world jerks to a halt and somehow it seems exactly the same way it was before the big revelation. But that can’t be, it can’t be because everything is going to be different now. 

They don’t speak as they trudge back to their father’s house and go their separate ways changing out of uncomfortable suits before finding each other in the kitchen. Gabriel won’t look him in the eye and Cas doesn’t know what to do about it. 

“I’m gay,” he blurts. Gabriel jerks and grips the countertop as though someone slapped him. “No one here knows that. I wasn’t ever brave enough to tell Dad.”

“Oh,” Gabriel chokes out. 

“I’m leaving here,” Cas explains as he creeps closer. “I only stayed because he was sick. I hate it here. It’s too small and everyone knows everything about everybody. I want to go somewhere bigger, where nobody cares about who I am or who my father is.”

“Vegas is like that,” Gabriel says numbly. “You could be anyone there.”

“Do your friends there know you have a brother?” Cas asks as he slides up beside where Gabriel’s knuckles are turning white on the countertop. 

“No,” Gabriel admits as he hangs his head. “I told them I was an only child.”

“Do they know you’re gay?” Cas asks as he presses closer, staying just out of reach.

“Sure,” Gabriel snorts. “No one cares about that.”

“Maybe when you go home you could bring your new boyfriend home with you,” Cas whispers as he reaches out with trembling fingers to stroke along Gabriel’s arm. 

“Cas?” Gabriel asks as he turns fearful eyes toward his brother. 

“You aren’t the only one who’s been wanting,” Cas answers as he takes the last step that leaves them pressed tightly together. “Don’t leave me again.”


	33. Date 33: Drive-in Movie

Title: Date 33  
Author: Gedry  
Pairings: Gabriel/Sam  
Rating: PG - 13  
Word Count: 592  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Drive-in Movie. 

Date 33

“The sound is horrible,” Sam complains. 

Gabriel laughs, “It’s the nostalgia we’re here for, not the quality control.”

“Tell me again why you like this?” Sam asks as he settles his too big body into something as close to a comfortable position in the extra small car Gabriel has.

“Everything is so high tech and super fast these days,” Gabriel sighs. “I mean, I know you are Mr. Computer with your job with the Geek Squad and your love of now toys. But sometimes I think as we gain global connectedness we lose personal connectivity.”

“What do you mean?” Sam asks. This discussion is frankly a hell-of-a-lot more interesting than the movie he can barely hear. 

“I mean,” Gabriel turns toward him, giving Sam his full focus. It doesn’t happen often enough for Sam’s tastes. “That back in my grandfather’s day he people in the neighborhood used to sit out on their front porches and watch the kids playing. If someone got in trouble or something bad happened the whole neighborhood was there to help out. Now, we all sit in our houses, behind closed blinds, worried about what our on line friend in Madrid is doing more than what’s happening outside of our house.”

“But global connectivity allows us to know what’s happening internationally,” Sam argues. “Those international issues impact our lives and our well being too.”

“I’m not saying they don’t,” Gabriel agrees with a dismissive wave of his hand. “Our online friends in Madrid are important to us. Being aware of global issues is a GOOD thing. It is. We should all be more aware. But we should also unplug for an hour or so a night and make sure the neighborhood we live in isn’t burning down around us.”

“Because you’re so good at doing that,” Sam teases.

Gabriel’s glare in return kind of surprises Sam. “Mr. Whitlock, who lives across the street?” Gabriel says and Sam nods. “His wife has stage four breast cancer. They don’t have any children. I changed my work schedule so I would be off on Wednesdays so I could drive them to her chemo appointments. Mrs. Marshal, who lives next to them? Her son’s autistic. I spend an hour with him on Sundays teaching him to skateboard. He’s getting really good.”

“Gabriel,” Sam whispers. He’s stunned and frankly trying to stop the tirade. 

“Mr. Singer’s wife died three years ago,” Gabriel keeps going. “I bake pies for him at least once a month and your older brother is helping him fix up his beat up old truck. The thing is a classic but you would never know it by looking at it.”

“I get it,” Sam comments as he waves his hand sin the air. “I’m sorry.”

“No you don’t, Sam,” Gabriel huffs. “You don’t get anything. If you got it, if you pulled your head out of internet land for half a damned second, then you would see all kinds of things that you’re missing. Like the fact that your best friend is fucking in love with you.”

“You’re my best friend, Gabriel,” Sam points out, stunned.

“Yeah.” Gabriel mumbles. “I know.”

“Well, if you know everything,” Sam exclaims with a grin. “Did you know I love you too?”

The look on Gabriel’s face is priceless.


	34. Date 34: Gondola Ride Venice

Title: Date 34  
Author: Gedry  
Pairings: Gabriel/Sam  
Rating: PG - 13  
Word Count: 895  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Gondola ride Venice. 

Date 34

The water laps against the side of the gondola as they make their way lazily through the passageways that surround Venice. 

“This is amazing,” Sam whispers as he watches the city go by. “Thank you for sharing this with me.”

Gabriel smiles, his skin lit golden by the fading sunlight as it dips below the buildings behind him. He looks heavenly for a moment and Sam feels his stomach do a flip flop before a sweet, warm feeling makes its way through his veins until his fingers tingle. 

He’s in so much trouble with this guy. He wants Gabriel so bad. 

It’s hard to believe that they stumbled into each other on business in this fantastic city. Especially since Sam wasn’t even supposed to be the one that went on this trip. He was substitute after the original lawyer who was supposed to come negotiate with Gabriel Novak backed out due to some kind of emergency. 

“Thank you for coming with me out here,” Gabriel replies. “I know it’s unconventional to do business this way but I’ve had all I can take of offices and board meeting for this trip. We’re in Venice for fucks sake. There should at least be the illusion of romance if you can’t accomplish it for real.”

It’s an interesting comment. “So which is it for us?” Sam asks with a guarded look in the other man’s direction. “An illusion or reality?”

There’s silence for a while as Gabriel looks out over the horizon as if he’s thinking about something personal, something that makes him a little sad. 

“I told your firm I would only do business with you,” Gabriel admits finally. 

Sam’s stunned. He knows he must look stupid with his eyes wide and his mouth hanging open but he can’t seem to pull himself together. “Me? Why?”  
“Have you looked at yourself?” Gabriel snorts. “You’re like an Adonis. I saw you leaving the building the last time I went to Milwaukee for a meeting. I couldn’t get you out of my head. So when they wanted to finalize this deal I told them to send you or it was a no go.”

“So, what?” Sam stammers. “My company getting a closing on this deal with you is dependant on me putting out? I hate to tell you, it’s not going to happen.”

“Your company is very invested in my agreeing with this deal, Sam,” Gabriel warns. “I think you might be underestimating your importance in the bigger scheme of things.”

“Fuck the company then,” Sam blurts out. “If they think I’m going to whore myself out for them then I can find another job. Tell him to pull this boat over. I’m getting out.”

“You have no idea where you are,” Gabriel comments. “You don’t speak the language. What are you going to do?”

“None of your fucking business,” Sam snarls. His chest hurts. He liked this guy. They had been having fun. He had thought maybe there was something between them and for it to have all been a lie, for it have all been business is too much. He wants out. 

“Your morals mean that much to you?” Gabriel asks. 

“Yes!” Sam exclaims. 

Gabriel’s gaze is assessing when Sam turns back to face him angrily. “The papers for the deal were already signed before the plane landed. I faxed them back this morning.”

“If that’s true then why make me think I was here for a good lay?” Sam crosses his arms and sits back. “Is this some kind of sick game for you?”

“I’m very rich,” Gabriel says calmly. “Dating is…..complicated for me. People are interested in me sometimes for not so nice reasons. I’ve been burned before.”

“So it was a test?” Sam asks. “You wanted to see if I would give in to keep the deal.”

“Yes,” Gabriel admits. “I needed to know you had morals. A relationship with me will be difficult. I travel a great deal and I need to have faith in my partner. I need them to have faith in me. I’m not looking for a fling here, Sam. I’m looking to settle down with someone. I’m hoping that someone might be you.”

“So I’m just supposed to get over this?” Sam questions. “Just supposed to go on with the rest of this date like you’re not insane?”

“Is this a date?” Gabriel asks. “If it is then I’m doing better at this than I thought.” 

Sam watches the water lap against the side of the gondola for a long time before he mutters. “I don’t even kiss on the first date.”

“I can wait,” Gabriel assures him. 

“I’m still pissed at you,” Sam comments even as he scoots a little closer to Gabriel’s side. 

“It won’t be the last time I tick you off,” Gabriel chuckles. 

“I’m sure,” Sam snorts. Gabriel’s hand is warm against his knee when the other man puts it there gently. It’s welcoming, Sam smiles as that warm feeling flares up again making him shiver. 

Gabriel leans into him fitting against Sam’s side like he belongs there.


	35. Date 35:  Double Date

Title: Date 35  
Author: Gedry  
Pairings: Gabriel/Sam, Dean/Cas  
Rating: PG - 13  
Word Count: 576  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – double date. 

Date 35

“Tell me again why Cas got to pick the place we went for our date?” Gabriel asks as he wipes sweat off his forehead. 

“He won the coin toss,” Sam reminds him with a shrug. “It’s not so bad.”

“We’re on safari,” Gabriel exclaims dramatically. “Lost out in the wild with no hope of making our way back to civilization.”

“We’re in the state park,” Sam chuckles. “You can still see the car.”

Gabriel glares at the Impala like she’s personally offended him. “Yeah okay…I’m hungry.”

“There are M&M’s in the car,” Dean says over his shoulder from where he’s making his way across a creek behind Cas. 

Gabriel turns to Sam with a scrunched up face and asks, “Why am I on a date with you when your brother is the one that packs the candy?” 

“Because you want me for my body,” Sam offers with a shrug. “I’m used to being a sex object.” 

He’s a little shocked when Gabriel doesn’t just laugh in his face. They’ve been friends for a long time, the four of them. It’s not like the attraction between them is new, it’s more like the tone of their friendship has changed to include a new color scheme that none of them had really thought was possible. 

Sam had thought he would wading through the summer, hanging out with Gabriel, Cas, and Dean with the bitter feeling of regret coiling in his stomach. Instead, Cas had cracked and thrown himself at Dean, literally, last Saturday. Once Sam had seen them so happy it hadn’t taken much a push to make him offer himself to Gabriel in the hopes that maybe he hadn’t been imagining his friend watching him a little more than he really needed too. 

He’d honestly been shocked when Gabriel had agreed. 

“Sammy,” Gabriel says quietly, shocking Sam back into the present. “You have no idea of all the things I want you for.”

The open longing in his tone makes Sam reach out and touch Gabriel’s cheek. It’s a moment; they’re having a moment, and Sam leans in to kiss Gabriel the same time they both hear a splash and a squawk of irritation from Cas. They jerk apart and turn to find their very wet brothers sitting in the creek.

The moment’s gone but Gabriel keeps their fingers tangled together as they both go over to make sure everyone is okay. 

“I told you,” Cas says grumpily. “Making out on a rock is not a good idea.”

“What if getting you wet was the whole idea?” Dean teases as he stands and tries to ring out his shirt. 

“Was getting yourself wet also part of the plan?” Cas ask as he shakes his head to get some of the water out of his hair. 

“Maybe,” Dean snorts. “I have a boo boo,” he offers as he holds out his scraped elbow. “Want to kiss it better.”

Cas gives him a displeased look that makes Sam and Gabriel giggle. But he grabs onto Dean’s arm and tugs him closer, kissing him possessively on the lips. 

Sam’s pretty sure Dean’s forgotten all about his elbow by the time Cas is done.


	36. Date 36:  Arguing

Title: Date 36  
Author: Gedry  
Pairings: Gabriel/Sam  
Rating: PG - 13  
Word Count: 621  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Arguing. 

Date 36

“We can go dutch,” Sam offers with a nod like he’s solved the problem. 

“Who the hell even says that anymore,” Gabriel huffs. “Besides, it’s not a date if we both pay for our own meals. It’s just two guys going out to eat together.”

“I can’t afford it this week,” Sam’s coming close to whining and he knows it. 

“So just let me pay,” Gabriel complains. “Why are you being so difficult about this?”

“Because I ask you out, not the other way around,” Sam sighs. “I should pay. Maybe we can just reschedule or something.”

“NO!” Gabriel blinks wide eyes like the vehemence of his disagreement to Sam’s latest insane idea surprises even him. He settles his shoulders with a little less tension before admitting, “I don’t want to wait another week.”

“You haven’t waited this week yet,” Sam snorts. “I just asked you out ten minutes ago and we’ve been fighting ever since.”

“I’m not hard to get along with,” Gabriel snaps. “I’m not. You’re just being unreasonable and if you could just be less rigid then you wouldn’t think I was the one with the problem.”

“You think I’m being rigid?” Sam gasps. “You’re the one being an idiot about this. I’m trying to be realistic. Not everyone in the world lives in a castle by the sea, Gabriel.”

“It’s not a castle,” Gabriel corrects with his finger pointing into the center of Sam’s chest. “It’s just a really big house. Besides it’s not like it’s my house. I can’t help what my parents do for a living”

“Maybe this isn’t going to work,” Sam groans. “We just come from two totally different places.”

“We’re in the same home room,” Gabriel barks. “How different can our worlds be? You’re just too sensitive about it.”

“First I’m rigid, now I’m overly sensitive,” Sam growls as he glares at the other boy. “Why did I ask you out in the first place?”

“I don’t know,” Gabriel murmurs. “But I’m really glad you did.” 

“Oh,” Sam breathes as they stare at each other. “Oh…”

Gabriel’s touch against Sam’s chest is hesitant. It’s like he’s not sure if Sam really wants him there, that close. Gabriel’s an idiot, Sam would love him a lot closer he just needs to prove he can pull his own weight. 

He wants to be an equal.

“Can you drive me home?” Gabriel asks after he presses his fingertips against Sam’s shirt unmoving. “I missed my ride meeting you here.”

“Where’s your car?” Sam asks. 

“I don’t have one,” Gabriel admits with a blush. “It’s sort of a communal vehicle that we all share. Today’s not my day.”

“I have a car,” Sam says with a smile. Dean gave him the Honda when he bought the beat-up Impala to rebuild. 

“That’s why I’m asking for a ride,” Gabriel says with a grin. 

Sam has a car and Gabriel doesn’t….this evens the playing field a lot between them. 

“How about this,” Gabriel offers. “You drive me home and in return I’ll make us dinner. We call it even and this can be our first date. We can spend the time trying to make a plan for the next one.”

“You want a second date with me?” Sam’s not going to be able to wipe the grin off his face for a year. 

“I want a lot of things with you,” Gabriel says with a wink. 

They hold hands while Sam drives him home.


	37. Date 37:  Ice Cream

Title: Date 37  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 557  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – ice cream. 

Date 37

“Caramel Biscuit?” Dean says slowly, like he’s tasting the words as the roll off his tongue. “That is a stupid name for an ice cream.”

“Like Rocky Road is better,” Cas huffs before swiping his tongue along the edge of the cone in his hand before it can drip. 

“Rocky Road is a perfectly acceptable name for an ice cream, thank you very much,” Dean glares at his friend out of the corner of his eye. 

“You would think that,” Cas snorts. “I bet you’d like it better if they had something called Road Rage, or Burning Rubber.”

“Shut up,” Dean orders as he bumps their shoulders together before catching a drip off his own cone prior to it landing on his pants. “You don’t know what you’re missing.”

Cas laps at his ice cream for a long moment while he looks off into the setting sun on Bobby’s back porch. Days like this are rare for them with their busy schedules. Dean’s always working and Cas is in school. They hardly have time to hang out anymore and Dean misses it a lot. He misses Cas. 

“I wouldn’t be opposed to a trade,” Cas offers quietly. “I’ll try your ice cream if you partake of my confection.”

“You make it sound so complicated,” Dean grumbles as he scoots what is probably an unnecessary inch closer. But what the hell, Cas has no concept of personal space and truth be told, Dean likes the feel of him pressed close. “Just hand it over.”

But Cas’ too blue eyes narrow as he turns to face Dean. He holds out the cone but maintains his grip, refusing to let Dean remove it from his hand. “Just try it,” Cas rumbles, deep and dark as he hovers the cone just to the side of Dean’s mouth. 

Dean hesitates…but then comments, “If you shove that thing up my nose I’m going to be so pissed.” 

He licks it, tentatively at first but once he realizes the flavor is good he takes a broader swipe with his tongue before making a pleased sound in his throat that Cas immediately mimics. Dean doesn’t think it has anything to do with the ice cream and Cas looks utterly shocked himself. 

They blink at each other for a moment until Dean says, “Not bad, but you’re going to drip.”

Cas startles and works his way around the cone like a professional, ensuring no more issues with the ice cream and his clothing. 

If Dean’s dick got any harder he thinks he might pass out. 

“You should try it again,” Cas offers as he holds it back out with trembling hands. “Just to be sure you like it.”

Dean grabs his wrist this time and nods before leaning in and licking the flavor right out of his friend’s mouth. 

Dean’s Rocky Road hits the grass behind the porch as it falls out of his numb fingers. 

Cas’ cone makes a squishing sound as it plops onto the crotch of Dean’s jeans. 

It takes them both a long time to notice.


	38. Date 38:  Sushi

Title: Date 38  
Author: Gedry  
Pairings: Gabriel/Cas/Dean  
Rating: PG - 13  
Word Count: 609  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Sushi. 

Date 38

Cas making dinner has always been kind of iffy at best. So when he announces that he wants to cook for their little Dean experiment Gabriel has a moment of panic that makes his heart pound and his palms sweat for entirely the wrong reasons. 

Then Cas starts talking about sushi and Gabriel lets the tension drain out of his body with a sigh. Cas can’t cook worth a shit, but you don’t cook sushi so at least the building won’t burn down. 

It turns out that Dean’s a fan of sushi. Gabriel thinks it’s kind of funny being that Dean lives mostly on burgers and extra greasy french fries. But he shrugs like it’s no big deal when Gabriel asks him about it as they sit down to eat; muttering something about his adopted father having a taste for it every so often and Gabriel lets it go. 

Dean’s kind of an enigma wrapped in a mystery, served with a side of bacon; a little salty but always awesome. 

It’s awkward as hell for the first hour. Dean sits in between them while Cas and Gabriel try to setup boundaries for themselves without making it too obvious or stepping on each others toes. It’s not working. After all how often to two brothers find themselves interested in the same guy. 

Even less likely that said guy would be interested in both of them. But Dean is…very much so, so much so that he’s found it impossible to tell which of them he likes more. 

So they decided to try sharing. Gabriel’s picking up the plates for a refill while Cas is cutting up some more things to eat. 

He almost cuts his own finger off in the process. Gabriel knew letting him make dinner was a bad idea. 

They end up huddled in the too small bathroom while Dean holds Cas tightly to his side and Gabriel does his best to disinfect and bandage the seriously cut index finger. Thankfully, they won’t have to end the date early to go to the ER. 

When he looks up from his ministrations Cas has his face pressed into the side of Dean’s neck and the way the other man is petting through his brother’s hair strikes Gabriel suddenly with the feeling of being an intruder, of pressing himself in where he doesn’t belong and isn’t wanted. 

So that’s how it’s going to be then, Cas-and-Dean with Gabriel pushed off to the kiddy table. He swallows the ache in his chest and squares his shoulders before turning to remove himself from the bathroom and grab his coat to leave and give the two lovebirds some privacy. 

Its nobodies fault, sometimes things just don’t work out the way you plan. 

But Cas’ bandaged hand is suddenly pressed against his cheek and when Gabriel turns his brother, still pale and looking shaky, is pleading with him silently not to run away. Dean’s free hand comes out to tangle in Gabriel’s hair and while his brain is still numb and unable to understand what’s going on Dean pulls him in close and Gabriel finds himself pressed against the other side of Dean’s neck. 

Cas slides his arm around Gabriel, pulling him in closer. Dean gives them both a squeeze. Gabriel lets out a bark of startled laughter. 

Maybe he needs to let Cas cook more often.


	39. Date 39:  ER

Title: Date 39  
Author: Gedry  
Pairings: Gabriel/John  
Rating: PG - 13  
Word Count: 626  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – ER. 

Date 39

“Winchester!” Gabriel calls out across the busy ER waiting room. It’s eight o’clock on a Friday and the busiest time of the shift for them. The place is crowded, full of people who either waited too long to see their primary doctor, don’t have one in the first place, or had an emergency. 

It becomes clear pretty quickly that Winchester, D. falls into the last category. The kid’s arm is bent at a really odd angle. 

“That’s us,” the man walking across the room with the boy says. “This is Dean. I’m John.”

“My name’s Gabriel Novak,” Gabriel offers with what he hopes is a reassuring smile. Winchester, J. is handsome. It’s too bad he has kids. 

Gabriel has always had a thing for rugged men…it sucks they are usually straight.

“Can you tell me what happened?” Gabriel says to Dean. 

The kid glares at him for a second before biting his lip and shaking his head. 

“Yeah, Dean,” John prompts. “I want to know what happened too.”

“I fell,” Dean mumbles. “That’s all.”

Gabriel catches John’s eyes from over the boys head and the man shrugs before offering, “I was working late at the garage when I got the phone call. The sitter said Dean and Sam came back in from playing outside and Dean’s arm was like this. I left work and picked them up. We came straight here. Neither of them will say how it happened.”

“It’s no big deal,” Dean grumbles. But quick examination and a few x-rays prove him wrong. The arm is broken, a hairline fracture. But the tendons and ligaments are strained badly. It’s like someone twisted his arm hard. 

Gabriel lets the doctors do their thing but when he’s told to call social services for a case review he puts his foot down. John Winchester is a gruff guy but he’s obviously a caring father. His younger son, Sam, has only left his arms a few times as John has reached out to hold onto Dean when he flinches away from some of the required procedures. The kids are obviously not afraid of their dad. 

“I’m sorry,” he offers weakly as the other nurse on shift calls anyway. “It’s part of our standard procedure.”

“I understand,” is John’s curt reply. But Gabriel knows he’s offended. Hell, he would be too. 

“I hate you,” Dean erupts from the bed as Gabriel brings him another blanket. “You got my dad in trouble.”

“Dean!” John barks. “He’s doing his job.”

“Gordon did it!” Sam blurts from John’s lap. 

“SAM!” Dean snaps. It’s clearly a brotherly confidence being broken. Gabriel knows that look; he has enough brothers to know it very well. 

“Shut up, Dean,” Sam huffs. “Gordon was picking on me. He shoved me down the hill. Dean tried to stop him but Gordon’s bigger and he twisted Dean’s arm.”

Three hours later The Winchester clan is on its way out the door. Gabriel assuring John that once the social worker double-checked Sam’s story with the sitter everything was in the clear. 

“Thank you for everything,” John comments as he walks toward the door. “We should have lunch or something.”

“You don’t owe me anything,” Gabriel says with a smile. 

“I never said I did,” John chuckles. “But you’ve been staring at me for hours and you’re pretty easy on the eyes yourself. I thought maybe we could see if there’s more than staring in our future.”

Gabriel writes his name and number on Dean’s cast.


	40. Date 40:  Fishing

Title: Date 40  
Author: Gedry  
Pairings: Sam/Cas  
Rating: PG - 13  
Word Count: 607  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Fishing. 

Date 40

“You enjoy this?” Sam asks after about an hour perched silently on the edge of the river bank near the back of his school. 

Cas doesn’t answer for so long that Sam’s about to repeat himself when his brother’s best friend finally says, “Not really.”

“Then why are we out here?” Sam sputters. This had all been Cas’ idea in the first place. He had discussed at length the fun he thought they would have fishing and Sam had caved and said he would go. Grant it, he had mostly agreed because he liked the idea of some personal time with his big brother’s number-one wing man more than he liked the concept of fishing. Cas is gorgeous and accessible in this weird-ass way that Sam’s still trying to figure out. 

They’ve known each other for years but it’s only been since Sam’s turned fifteen that he started paying attention to the way Cas’ eyes shine in the sunlight or the way his ass looks in his jeans. 

At eighteen Sam’s pretty much comfortable with the idea that he has the hots for Cas. Maybe more the hots honestly; Cas is intelligent and focused. Sam’s turned on by the whole package. 

He just needs Dean to not find out. How do you explain to your brother that you want to touch his college roommate so bad you think you might die?

“Dean,” Cas answers after another long pause. 

“Dean hates fishing,” Sam coughs. 

“Exactly,” Cas answers with a smile. “You and your brother are too much alike in some ways. Do you have any idea how long it took me to think of an activity that I could talk you into doing that Dean wouldn’t immediately want to come with? It was so frustrating.”

“Why wouldn’t you want him to come?” Sam asks. He’s lost. 

Cas fixes him with a stare that makes Sam’s throat and his pants feel tight. “Sam,” he says in this extra low gravelly voice. “I thought maybe we should spend some more time alone together. If you’ve decided that’s something you might want to do.”

It hits him suddenly, Cas knows. Cas knows Sam’s been lusting after him for years and years. Sam had been so worried about Dean finding out that he hadn’t taken a second to worry about Cas himself at all. 

“Oh fuck,” Sam feels the words fall off his suddenly numb tongue before he can stop himself and then groans in horrified embarrassment. “You must think I’m so kind of idiot. I’m sorry Cas. I’ll just leave you guys alone. You didn’t have to make this whole fishing thing up just to take me out here and break it to me gently. I appreciate you not telling Dean though.”

Cas is watching him with this expression of dazed curiosity that Sam has only seen on him a few times before. He’s stumbling to his feet, getting ready to run away from this moment of exposure when Cas announces, “I hate fishing. Want to make out instead?”

“With you?” Sam asks dumbly. 

“Unless you like kissing fish,” Cas chuckles. But when he tugs Sam back to the ground the touch he uses against Sam’s wrist is gentle, warm, safe. 

He smiles and Sam can’t help but return it with one of his own before leaning forward and deciding to press his luck.


	41. Date 41:  Amusement Park

Title: Date 41  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 532  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – amusement park. 

Date 41

“Dean…” Cas begins warningly as the rollercoaster they stood in line for an hour to ride is finally creeping it’s way to the first drop. “I want to get off now.”

Dean can’t stop the bubble of nervous laughter from bursting out of his mouth. God knows, he’s been having the same thought himself as he sits here, pressed against the back of the seat, afraid to move or open his eyes because he hates heights so much. “I don’t think that’s an option, Cas.”

“Please..” Cas whispers and it’s the edge of panic in his voice that makes Dean pry his locked hand off his handle bar to reach over and press it against Cas’ shaking hand. 

“I’m right here,” Dean assures him. “It will be fine.” 

Except they must be at the top now because Cas makes this noise like a goat being strangled and then for one blissful moment the clinking noise the cars have been making stops before the people in the row in front of them start to scream. This is it, they’re going over. 

Dean’s going to die. See, it’s not really flying he hates. It’s falling that bothers him. 

He screams like the great big sissy girl he will never admit to being. His head thrown back and tears leaking involuntarily from his eyes. Cas is screaming right along with him so Dean’s pretty certain that at least he won’t have to worry about his date making fun of him for shrieking when this is all over. 

Oh God! They’re never going to hit the bottom. How long is this drop? Dean’s stomach hits the back of his throat and he just prays he doesn’t puke. 

How bad would that be on the first date?

They finally shift into the next drop but it’s smaller, more manageable. The loop-to-loop next and on the way down the far side of that part of the coaster he hears this really odd sound from the other person in the seat with him. 

Cas is laughing. 

Cas, reserved, focused, serious, doesn’t understand humor at all and hates when people tell jokes, Cas is laughing his ass off. 

Dean’s mouth drops open in shock before they swerve around the next curve and he snaps back into himself but there’s a smile curving around his mouth. Maybe this rollercoaster isn’t so bad. 

When they pull into the station he turns to look at his date. Usually tense Cas is sprawled, weak and smiling in the seat next to him. He looks at Dean with so much joy in his eyes that Dean’s a little dazed by it and Cas has to tug on his hand to get him down the ramp. 

“That was fun,” Dean announces as they stop to decide where to go next. 

Then he has an armful of Castiel and he’s being kissed and kissed and kissed. 

They should probably ride it again.


	42. Date 42:  Third Time's the Charm

Title: Date 42  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 685  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – 3rd time’s the charm. This is Dean’s side of the story from Date 15. 

Date 42

He’s loved Cas forever, or at least as long as he can remember. At first Dean had thought he loved him like a brother; but he never wants to be as close to Sam as he does to Cas, never physically aches to touch him. 

Cas is in a different category than brother or friend. 

Dean’s been waiting, waiting for the right time and for Cas to give him some kind of sign that maybe Dean’s more than just ordinary to him too. 

When it happens it’s so totally not what Dean was expecting. He thought the music would swell or there might be frantic, uncoordinated kissing. 

Instead Cas just blurts, “I think I love you,” out while Dean’s in the middle playing Halo one night. He had muttered back a very unfocused “love you, too,” before he even really took the time to think about what was happening. 

Cas had gone home with a smile on his face that night but Dean sort of thought he needed to make it up to him. 

On their first date Dean took Cas out to dinner at the Thai place he’s been talking about for six months but could never afford to go eat at. He’s going to have to work overtime to pay for gas for next week but it was worth it to watch Cas expound on each individual dish they shared in his excitement. Cas rarely gets excited like that. When Cas had pressed up close against him in a quick half-hug after Dean had driven him home it was kind of shocking. 

That’s right, they can touch and hold and kiss now. 

Their second date was derailed by a family fight that happened right before Cas left to come see Dean. His friend had shown up shaking with tension and where before Dean would have just played it off because he couldn’t risk Cas finding out that Dean wanted him, he realized he didn’t have to do that anymore. 

It had only taken a bit of convincing to get his new boyfriend sprawled on his stomach topless across Dean’s bed. Dean sat beside him and used what was probably a half a bottle of lotion to work the tension out of Cas’ neck and back. By the time Dean was done Cas was asleep and there was nothing to do about it but to squeeze in behind him and hold him close. 

When Dean woke up later Cas was gone. But Dean still has the little note Cas left him pressed into his favorite book in his room. 

Thank you, Love you. Cas. 

So by the third date Dean’s pretty desperate. He wants a kiss and he wants it tonight. Dinner was nice and the movie was fun. They hover outside Cas’ house leaned up against the Impala as they joke and flirt and just enjoy each other. When it’s time to go Dean’s already leaning in when he sees Cas’ lips part. Their legs bump and Dean’s pulse goes through the roof. 

Cas is hard, because of him, for him. 

What was supposed to be a peck turns into a bone-meltingly hot event. Cas is strong and he just keeps dragging Dean in closer and harder as he grinds up against Dean’s hip and makes these totally delicious mewling noises. It’s by far the best kiss Dean’s ever had and he is the only person Dean wants to ever kiss again. 

When he pulls back Cas tries to follow him, their noses bump and it’s so hard not to just put his friend back in the car and drive him away somewhere they could just be together. 

But they always have tomorrow and this is all so very sweet. Dean just wants to drink it up.


	43. Date 43:  Kissing in the Rain

Title: Date 43  
Author: Gedry  
Pairings: Dean/Cas  
Rating: PG - 13  
Word Count: 576  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Kissing in the rain.

Date 43

They’re both soaking wet. That’s what happens when you lock your keys in the car on the last day of school in the middle of spring. Dean looks across the roof at his already slightly damp college roommate and shrugs. 

It’s going to be a long, moist, walk home. 

They take the short cut that leads them through the quad and past the gym. The campus has more hills on this side but the road is less busy and they’ll see less people while they try to make it back to their apartment. 

Dean tugs his jacket a little tighter against his neck until he realizes it totally doesn’t matter. It’s pouring so hard it’s running down the inside of his coat and soaking his shirt. 

Cas doesn’t even try. He strolls along at Dean’s side as though he planned for this to happen, like the cool water drenching his jeans and t-shirt under his trench coat was expected and even welcomed this afternoon.

Dean slips on the steps headed down to the next parking area and after that they’re holding hands. 

He starts walking slower; no longer feeling the cool afternoon breeze or the glinting sun on his head. He’s only aware of his friend’s warm body bumping into his every time they take a step and the fact that Cas looks so good wet all over. 

Oh, fuck. He’s in love with his roommate. 

“Your freckles standout with you damp like this,” Cas rumbles as they stand frozen in the middle of the residential street they were crossing when Dean had his epiphany. 

Dean flushes pink notes that it probably just makes his stupid freckles that much more noticeable. “They kind of suck,” he mutters. 

“I like them,” Cas comments softly as he wipes at his face with his free hand to clear off some of the rain. “You’re very attractive.”

“You can’t just say shit like that, Cas,” Dean warns even as he shakes his head with a smile. “We’ve talked about this. People will get the wrong idea.”

“What if they get the right one?” Cas questions as he reaches up to cup Dean’s chilled cheek. “What if it’s you that has the wrong idea and they’ve been right all along?”

Fuck it, his book bag is already soaked and his books are probably ruined. Dropping them in a puddle is the last thing he’s concerned about right now. Once the weight is off his shoulders it’s easy to reach out and grab the wet hair on the back of Cas’ head before dragging him in and closing the distance between their bodies. 

So hot…so perfect; Dean groans his appreciation as the other man cups at his ass through his soaked jeans before sliding up under his shirt to slip and drag against the dampened skin on his back. Cas bites at his lips and then soothes the impressions of his teeth with his tongue. Dean nips his chin and rubs his stubbled chin against Cas’ freshly shaven face. 

The car honking forces them apart; they are in the middle of the street. 

When they start running home, it’s not to avoid the rain.


	44. Date 44: Watching Porn

Title: Date 44  
Author: Gedry  
Pairings: Gabriel/Sam  
Rating: PG - 13  
Word Count: 686  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Watching Porn.

Date 44

“What are you doing?” Sam asks, slightly horrified, as he comes back into their apartment after class. 

“Watching porn,” Gabriel comments as he stays sprawled on the couch in front of their big screen plasma television. 

“I can see that,” Sam comments because Oh My God, he can’t see anything but that. “I’m asking why you’re doing it in the middle of the living room when you have a television in your room.”

“It’s for class,” Gabriel says flatly. “Not for pleasure.”

Sam sighs; Gabriel is a psychology major with a special focus on research directed toward human sexuality. So, sometimes, when Sam comes back from a plain old run of the mill legal course he finds the coffee table riddled with vibrators or cock rings. Occasionally, there are six different kinds of lube labels on the kitchen table. One time, last semester, Gabriel took a running research poll of everyone who lived in their apartment complex related to their personal kink factor. He had gotten slapped twice, punched once, and kicked in the nuts. 

Sam had spent a long night fetching him icepacks. 

“Gabriel,” Sam grumbles as he drops his book bag. “We talked about you leaving your crap all over the place. Take the porn to your room.”

“I can’t,” Gabriel complains. “I’m researching if the size of the screen impact arousal. My TV is too small.”

Sam’s silent for long enough that the girl on the screen moans her way through what sounds like a very fake orgasm and rolls his eyes in irritation. 

Sam hates porn. It’s so staged and weird. Most of the time when he watches it half of his brain worries about whether or not the actors really enjoy it at all. 

For Sam, there’s nothing worse than not enjoying sex. Sex is supposed to be fun and intimate, awkward and stumbling; it’s supposed to be you at your most unguarded sharing yourself with another person that you love. 

Sex and love are firmly linked and inseparable for Sam. But he’s learned, living with Gabriel, he’s in the minority. 

He gives up and flops on the sofa next to his roommate. “How’s the research going?”

“I don’t notice a difference,” Gabriel sighs. He looks frustrated. “It stopped being entertaining like an hour ago.”

“Maybe the fun factor with you and casual sex is finally wearing off,” Sam teases. He might be a serial monogamist but Gabriel is his exact opposite. Gabriel hates relationships. To him sex is the whole point of meeting people. The emotional connection that might come with the physical act is to be avoided at all costs. 

“That would be horrible,” Gabriel exclaims dramatically and flops over into Sam’s lap. “Hold me I’m scared.”

Sam reaches out to take the remote and turns off the TV. He leaves Gabriel draped across his lap and puts his arm down across his roommate’s chest in an affectionate half hug. It’s an odd kind of cuddling that happens more often than not these days. 

“You know,” Sam snorts as Gabriel snuggles closer. “If you found someone else to do this cuddling thing with they might give you sex too. You can have both worlds.”

“It would require dating,” Gabriel says with a look on his face like he smells something bad. 

“Relationships are worth it,” Sam chuckles. “I promise.”

“Prove it,” Gabriel says softly. “Have a relationship with me and put your money where your mouth is.”

Sam’s shocked. But honestly, Gabriel’s amazing. Sam would have jumped on him in a second if he had ever shown a bit of interest in anything more than a roll in the hay. “I don’t put out until I’m in a committed, monogamous, love filled relationship,” Sam warns. 

“Give me a chance,” Gabriel pleads as he brushes his fingers through Sam’s hair. “I want to make this something wonderful with you.”

Sam cooks dinner. They call it a date.


	45. Date 45: Juggling Torches

Title: Date 45  
Author: Gedry  
Pairings: Gabriel/Kali  
Rating: PG - 13  
Word Count: 666  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Juggling Torches.

Date 45

She’s power and regal energy wrapped together inside the swirling firelight. She’s unapproachable and irresistible, the way she carries herself like she’s touched by nothing but aching for something. 

She drives him crazy with her dark gaze and assessing eyes. She leaves him feeling lacking and wanting so much to prove to her that he could b everything that she needs, that’s she’s missing in her life. 

But he never gets the chance. 

Kali is one of the center pieces in this glorious act that they are both a part of. She’s a front runner, a treasured bit of artistry in the Cirque show that employs them both. A powerhouse of talent forged through hard work and dedication. 

Gabriel is a clown. 

Not that his title should fool you, Gabriel is talented in his own right and he can work a crowd into a frenzy with very little effort on his part. He knows he’s an important part of the show. He and his troupe fill in all the little bits and spots that the other performers leave blank during their transitions. 

He’s so good in fact that his character is the one assigned to Kali’s performance. He foreshadows her entrance and makes certain the crowd follows his attention as she moves about the stage. He is her assistant and number one fan for ever performance. And if he’s lucky by the end of their run she might know his name. 

It’s not that they don’t speak. He takes directions well. Honestly, if it were anyone else Gabriel would have handed anyone who spoke to him the way she has their asses by now. But when he’s around her he turns into this thirteen year old with sweaty palms and a raging erection. 

He can’t think straight. 

His friends think it’s hysterical. They tease him mercilessly about it. Bumbling idiot is not Gabriel’s style. Neither is he a hero, but that doesn’t stop him from rushing to her aid on evening when the torches she’s preparing to juggle burst into flames that are impossibly large. 

She’s burned, but not badly; a few blisters and some redness; nothing that will leave a scar. It takes Gabriel three weeks to limp back into work and his back still aches where the fire crawled up his back as he shielded her from the blaze. 

“Good luck with that bitch,” Lucifer comments as she runs him out of her practice area. 

Gabriel snorts; it’s the first thing that’s amused him in almost a month. 

“Gabriel,” she breathes as he comes around the corner. “You’re back? I’ve missed you.”

Yeah, right. He’s not that lucky. 

“I’m sure you’ve been kept entertained,” he offers as he sinks down onto his usual cushion with a wince. 

“They weren’t nearly as attentive as you,” Kali complains. But the she puts down her practice balls and comes to kneel in front of him. “You were hurt because of me.”

“I was hurt because whoever made those chemicals was an idiot,” Gabriel corrects her. 

“I would like to thank you,” she continues and there’s this softened look around her eyes like maybe this is who she really is and he’s just now getting a glimpse behind the mask. “Come to dinner with me.”

“You don’t owe me anything,” Gabriel says with a shake of his head. 

When she touches his hand he forgets what his argument for not agree to dinner was in the first place. 

“I’m…uncomfortable around people,” Kali says softly. “It’s hard for me to let people get close to me. I want to get to know you. Have dinner with me, please?”

Gabriel’s head is swirling. But he knows he says yes because her smile is blinding.


	46. Date 46: Superbowl

Title: Date 46  
Author: Gedry  
Pairings: Gabriel/Cas  
Rating: PG - 13  
Word Count: 667  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Superbowl.

Date 46

“OH MY GOD!!” Gabriel howls at the big screen Television. “They are just throwing it away!! I can’t watch this. I can’t. I’m going to be sick. Did you see that?”

“I’m sorry,” Cas sighs from his position on the love seat. “I’m afraid I wasn’t paying attention.”

“Seriously, Cas,” Gabriel grumbles. “Why the fuck are you even here?”

“You invited me,” Cas shrugs. “It seemed important to you.”

“It’s the SUPERBOWL,” Gabriel points out for the fifth time as though yelling it will make his brother understand its importance. “I mean, shit!”

“Yes,” Cas huffs. “I’m aware.”

“So weird,” Gabriel grumbles. “You have just always been so weird.”

“Again,” Cas snaps as he slams his book shut. “I’m aware.”

Gabriel watches his step-brother gather his things stiffly and look for his keys. He and Castiel have known each other for years. They went to the same middle and high school before college and had occasionally kept in touch even then. It was a passing thing. They weren’t exactly friends but not unknown to each other. After all, how could you ignore Cas? His blue eyes alone were enough to make certain you remembered him but add to that his super toned ass and long, elegant fingers and Gabriel was pretty much a hopeless case. 

Or he would have been if two things hadn’t stood in his way. The first being that Cas is totally oblivious to everything and everyone who crosses his path sexually. Gabriel’s never been able to figure out how to get an opening under his isolative armor. 

The second problem being that in their senior year of college Gabriel’s mother married Castiel’s dad, making them effectively related. 

Holy shit it’s been strange and painful. 

Gabriel’s never been so glad he has his own apartment. But it’s offered a strange opportunity for him to torture himself by spending more time with Cas. Sadly, the more time he spends with the guy the more Gabriel actually likes him. It’s like a double edged sword pressed snuggly up against his very blue balls. 

“Where are you going?” Gabriel asks as Cas finally produces his keys. They were in his pocket the whole time. 

“Home,” Cas comments as he starts picking up his stuff. “This activity is clearly not for me. I don’t understand the dynamics of why large men running after little pointed balls is entertaining.”

“Don’t go!” Gabriel blurts as he lunges to his feet. “It’s almost half time. I’ll switch it to the puppy bowl. You’ll love it. They have a kitty half time show.”

He’s going to hell, he knows it. But Cas has a thing for animals. 

“Alright,” Cas agrees. “I will stay through half time.”

Gabriel’s a little surprised when Cas sits down next to him rather than returning to the love seat but having the other man pressed so close is really nice and he sort of loses track of the game score or who he’s supposedly rooting for. 

“Gabriel,” Cas whispers some time later. “It’s half time.”

Gabriel jumps before reaching for the remote to change the channel. “You know,” Cas comments as he fumbles. “If I had been aware that my proximity would make you silent I would have started sitting next to you years ago.”

“So you just want me to shut up?” Gabriel asks. 

“And kiss me,” Cas offers with a smile way too wicked to be currently on his face. “I’ve been waiting a very long time for you to make a move.”

“Son of a bitch,” Gabriel chokes. “How long?”

“Years,” Cas chuckles as his dumbstruck expression. “Since before our parents met.”

It’s hours later before Gabriel realizes he’s missed the end of the game. 

There’s always next year.


	47. Date 47:  Left up to me.  Mini Golf

Title: Date 47  
Author: Gedry  
Pairings: Gabriel/Cas/Sam/Dean  
Rating: PG - 13  
Word Count: 534  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – was left up to me…..but I loved the suggestion of mini golf.

Date 47

“Gabriel!” Dean barks as he jerks away from the group of them for the third time. “If you slide that putter up my ass crack one more time I’m going to throw you in the lake with the giant goldfish. I swear to God!”

“Dean,” Sam hisses. “There are kids here.”

They all look around to discover that there are several couples and families now frozen on the green staring at the four of them. 

“So what?” Dean huffs. “This was your dumb ass idea anyway.”

“It’s been very educational,” Cas says softly from the back of the group. 

“You would think so,” Gabriel snorts. “How many hole-in-ones do you have so far?”

“Three,” Dean, Sam and Cas answer in unison.

“I’m a natural,” Cas adds with a proud smile. 

“You’re a ringer,” Dean accuses. 

“That would imply we’re playing for something,” Gabriel comments. “Are we?”

“Suggestions?” Dean asks. “I’m open.”

“Kisses,” Cas says firmly. “We’re playing for kisses. One for each hole-in-one.”

And yeah, okay…that makes this serious. They look at each other. Four pairs of eyes scanning to see if they’re ready for this step into the unknown. The four of them have this thing, something undefined and wild boiling up under the surface of their friendships. Something wanting and hot just ready and waiting to be exposed; they’ve flirted with it, glanced at it, but to move from a few too lingering touches into flat out mouth on mouth action is a little bit of a jump. 

It would make this serious, it would make this real. 

“I’m in,” Sam agrees first. Dean’s head snaps toward him and Sam shrugs. “Isn’t that the whole point of this date? To find out if we can make this work?”

“Good enough for me,” Gabriel says lightly. But the way he’s got his hands stuffed so far down into the pockets of his jacket prove just how uncomfortable he really is. 

“Yeah,” Dean nods. “I can do this.”

They go on with the game. Dean manages two hole-in-ones by the end. Cas rounds everyone out with five of his own. Sam and Gabriel don’t get any. Gabriel more because his attention span is too short for him to be patient enough to plan out his shots and Sam because he’s just too uncoordinated. 

In any case, they’re assuming they’ll be getting kisses either way. 

The drive back to Gabriel’s apartment seems incredibly long. The tension between them is palpable. But then the door is shutting and Cas is sliding off his coat before stepping into Dean’s arms. He stops at the last second before their lips meet to turn toward Gabriel and Sam and say, “Don’t go anywhere. I’ll be right with you.”

Dean laughs, low and deep before Cas presses their mouths together. Then no one’s laughing at anything and who knew Cas could kiss like that?


	48. Date 48: Living History

Title: Date 48  
Author: Gedry  
Pairings: Gabriel/Sam  
Rating: PG - 13  
Word Count: 713  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Living History.

Date 48

The clanking of the bells annoy the shit out of him but am grinds his teeth and forces his way through the pen full of dairy cows until he gets to the next row over where the farm opens up into sweeping countryside and clear fields. 

Gabriel’s crouched behind the barn gnawing on a candy bar as big as his own arm. 

“I don’t think those are allowed on the premises,” Sam teases. 

“Fuck you,” Gabriel snorts. “Turn me in. You can only ask a man to give up so much.”

“You’re seventeen,” Sam snorts. “You’re not even technically a man yet.”

“So says you, boy wonder,” Gabriel chuckles as he pats the ground next to him and breaks off part of the slightly melted chocolate bar in order to share it between the two of them. “I’m glad you came.”

Sam settles in, tucking his long legs under his body and leaning back against the old slowly rotting wood of the barn before answering, “You told me to meet you at the edge of hell for something sinfully good. I almost didn’t understand you message much less decide to come out here.”

“But here you are,” Gabriel shrugs. “So it worked out all the same.”

“I was intrigued,” Sam admits softly as he chews the contraband candy bar as slowly as he can. He has no idea where Gabriel got it from, much less why the wise mouthed little shit wants to share it with him, but Sam’s not looking a gift horse in the mouth. 

This fucking farm makes a juvenile detention facility seem like a spa. The judge gave Sam a summers worth of community service to be carried out at this throw back place off Route six that does it’s farming the way they used to do it back in the old days. No heavy equipment, no cell phones, no computers, no life outside of the care and upkeep of the animals and crops. 

It’s exhausting and Sam has to begrudgingly admit sort of educational. His roommate is Gabriel, who’s here until he turns eighteen in three more months. Sam has no idea what the guy did to earn that distinction but Gabriel’s been here longer than anyone and as far as Sam knows he’s the first person Gabriel’s ever shared his stash with. 

Of course, when the other kids whispered about Gabriel’s stash Sam was thinking they meant pot not candy. But hell, they one time he smoked pot it make him sick anyway. Sam loves chocolate. 

“What are you going to do when you get out of here?” Sam asks after a long pause. 

“Want to know a secret?” Gabriel asks with a quick glance in Sam’s direction. 

“Sure,” Sam tries for nonchalant. 

“I’ve been out for over a year now,” Gabriel grins. “The people that own this place adopted me after the judge said I was cleared. I didn’t have anywhere else to go so here I am.”

“So this is….home?” Sam’s dumbstruck. 

“It’s not so bad,” Gabriel chuckles as he waves another candy bar at Sam; one he seems to have produced with the snap of his fingers. “A little boring but being homeless with a psychotic mother and two little brothers to take of was a lot worse.”

“My dad’s an alcoholic,” Sam offers, wincing as he says it. “My brother practically raised me after mom died.”

“Maybe you should think about staying too,” Gabriel snorts. “They’re looking for someone to help with the books. Isn’t that close to what you got arrested for?”

“Hacking,” Sam shrugs. “It’s little different.” 

Gabriel grins at him again; his hand reaches out and smears a trail of melted chocolate around Sam’s wrist as Gabriel touches him softly. It makes Sam shiver, feels good in all the right ways. 

“So what do you do for fun around here?” Sam asks as he catches Gabriel’s hand and holds it. 

“Skinny dipping?” Gabriel offers with a smile and Sam just knows he’s totally screwed.


	49. Date 49:  All Hands

Title: Date 49  
Author: Gedry  
Pairings: Gabriel/Kali  
Rating: PG - 13  
Word Count: 570  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – All Hands.

Date 49

They stumble back up thee steps to her rat trap of an apartment, stopping in the stairwell just long enough for Gabriel to get his hands up the back of her blouse and unhook her bra. 

Her eyes roll up in her head as she tugs at his hair and the back of his shirt, the belt to his pants and the back pocket that his wallet isn’t in so that she can grope his ass before slipping back around to the front and cupping his cheek, his neck, tugging on his ear before searching for his nipple and tugging on it sharply until he moans greedily and finally steps back far enough for her struggle with her keys and open her door. 

“Jesus,” Gabriel pants as he mouths at the back of her neck while she drops her keys twice before finally….finally gets the door open and they almost fall through into her two room piece of shit. “Did you grow and extra pair of hands or something? I swear to go you’re still grabbing my ass.”

“I am,” Kali chuckles teasingly. “It’s a talent of mine. I should have mentioned that over dinner but I was too distracted by your dashing good looks and terrible sense of humor.”

Gabriel’s laugh really is adorable. If her panties weren’t so wet she might entertain the idea of tickling him until he peed or something just so that she could hear more of the delightful sound. But there is probably going to be time for that later. 

After all, this might be their first date but it’s not their first time. Friends with benefits can be a beautiful thing when they live just next door but when you start to spend more of your benefit time stroking your hands through is sweaty hair and enjoying the weight of his body against yours it’s time to get honest. 

Love’s funny like that, she guesses. You would think it would be old hat to them now but for some reason just the concept of knowing he values her not just her body makes her even hotter for him now. 

Kali wants him in the worst way. She just grateful he’s willing to go with the flow. 

“I’m not usually like this,” Gabriel says with a grin as he tugs on her hair gently. “Normally I don’t put out until the third date.” 

She’s still smiling when starts sucking on that spot on her neck that makes her crazy. There’s still the barest hint of a grin as he slides his trembling hands up under her skirt to tug down the thin straps of her panties before tossing them away to parts unknown. 

“But for you,” he whispers as he picks her up and carries her to her bedroom. “I’ll bend the rules.”

He squeaks like a dog toy when she pinches his ass the same time she drags her nails up his side before throwing an arm around his neck and kissing him senseless. 

“You really are all hands aren’t you?” Gabriel murmurs into her mouth. 

“You love it,” Kali assures him. 

She’s pretty sure he does.


	50. Date 50:  Disneyworld

Title: Date 50  
Author: Gedry  
Pairings: Gabriel/Sam  
Rating: PG - 13  
Word Count: 541  
Disclaimer: These characters do not belong to me. I am making no profit from this fanfiction.   
Beta: none  
Spoilers:  none  
Warnings: None.   
Summary: Written for 50 first dates – Disneyworld.

Date 50

“I can’t believe how much the food here costs,” Gabriel grumbles as he slides into the booth next to Sam. 

“I paid,” Sam reminds him as he picks at some of Gabriel’s fries. 

“What’s your point?” Gabriel questions as he bites into a burger like he’s been starving for days. 

Sam grins at his bliss-filled look. He’s also pretty happy Gabriel is sitting pressed close next to his side instead of across the booth from him. It’s nice; the warmth of the other man’s body seeping into his, Sam finds himself leaning closer, wanting more. 

Gabriel doesn’t disappoint him. He slips an arm under the table to slide it into the space between Sam’s arm and the side of Sam’s body. They end up tangled together in something like a secret embrace. It feels so good, like Sam’s supposed to be here right now, like he fits with Gabriel in a way he hasn’t ever felt like he fit before with anyone else he’s been with. 

It’s easy, which is kind of shocking because Gabriel’s not really an easy guy. He’s raised complicated to something of an art form but when Sam finally decided to take a risk on the other teaching assistant he’d been pleasantly surprised by the way Gabriel brightened and lightened and welcomed him in close. 

Like he wanted Sam there, like he had been saving a space for Sam for a long time and was relieved that he finally showed up to take it. 

“You’re kind of glowing,” Gabriel comments after he inhales his food. “It’s sort of sexy.”

Sam flushes ten shades of pink. “We’re in a diner at Disneyworld, Gabriel,” Sam hisses. “There are kids everywhere! You can’t just go throwing around words like sexy. Someone might hear you.”

“Sam,” Gabriel snorts. “Have you looked at yourself recently? I’m fairly certain everyone here knows you’re sexy. It’s a little hard to miss. You’re like ten feet tall.”

Okay, so Gabriel might have a point. Some of the mothers they’ve seen walking around the park have walked into walls and tripped over their kids trying to get another look at Sam. 

Gabriel’s watched it all with a tremendous amount of glee. 

“Where are we going next?” Sam asks, hoping to turn the conversation to something more socially acceptable. Does he want Gabriel? Hell, yeah. Is kissing Gabriel almost all he’s thought of since he met the man two months ago? Hell, yeah. But that does not mean that he’s going to ravage the guy in the middle of the happiest place on earth. 

“Tower of Terror,” Gabriel announces as he sucks down the last of his milkshake. “I want to see what kind of noises you make when the floor falls out from under you. A friend of mine swears it’s the same noise you’ll make during sex.”

Sam busts out laughing. “If you puke in my lap you’re walking home.”

Gabriel never un-wraps their arms on the walk over to the ride.


End file.
